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40963-14-2

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40963-14-2 Usage

Chemical Properties

Off-White Solid

Uses

2-Amino-2,3-dimethylbutyramide is an important intermediate in the synthesis of potent imadazoline herbicides. In addition, it is used to prepare new chiral ligands.

Check Digit Verification of cas no

The CAS Registry Mumber 40963-14-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,9,6 and 3 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 40963-14:
(7*4)+(6*0)+(5*9)+(4*6)+(3*3)+(2*1)+(1*4)=112
112 % 10 = 2
So 40963-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H14N2O/c1-4(2)6(3,8)5(7)9/h4H,8H2,1-3H3,(H2,7,9)

40963-14-2Synthetic route

2-amino-2,3-dimethylbutyronitrile
13893-53-3

2-amino-2,3-dimethylbutyronitrile

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

Conditions
ConditionsYield
With water In aq. phosphate buffer at 20℃; pH=7; Concentration; pH-value; Temperature; Solvent; Microbiological reaction; Green chemistry; Enzymatic reaction;97.3%
With ammonium hydroxide; dihydrogen peroxide
With sulfuric acid; water
ammonium hydroxide
1336-21-6

ammonium hydroxide

2-amino-2,3-dimethylbutyronitrile
13893-53-3

2-amino-2,3-dimethylbutyronitrile

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

Conditions
ConditionsYield
With sulfuric acid In ice-acetone
With sulfuric acid In ice-acetone
dimethyl 5-(1-acetyl-3-methyl-2-imidazolidinyl)pyridine-2,3-dicarboxylate

dimethyl 5-(1-acetyl-3-methyl-2-imidazolidinyl)pyridine-2,3-dicarboxylate

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

5-(1-ACETYL-3-METHYL-2-IMIDAZOLIDINYL)-2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL)NICOTINIC ACID AMMONIUM SALT
136592-75-1

5-(1-ACETYL-3-METHYL-2-IMIDAZOLIDINYL)-2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL)NICOTINIC ACID AMMONIUM SALT

Conditions
ConditionsYield
With ammonium chloride; potassium tert-butylate In chloroform; toluene100%
5-(1,3-dioxolan-2-yl)-2,3-pyridinedicarboxylic anhydride

5-(1,3-dioxolan-2-yl)-2,3-pyridinedicarboxylic anhydride

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-[(1-CARBAMOYL-1,2-DIMETHYLPROPYL)-CARBAMOYL]-5-(1,3-DIOXOLAN-2-YL)NICOTINIC ACID

2-[(1-CARBAMOYL-1,2-DIMETHYLPROPYL)-CARBAMOYL]-5-(1,3-DIOXOLAN-2-YL)NICOTINIC ACID

Conditions
ConditionsYield
In tetrahydrofuran100%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-nitrobenzyl chloride
610-14-0

2-nitrobenzyl chloride

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-nitro-benzamide

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-nitro-benzamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;98%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2,5-dinitrobenzoyl chloride
778-90-5

2,5-dinitrobenzoyl chloride

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2,5-dinitro-benzamide

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2,5-dinitro-benzamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;94%
2-methoxycarbonyl-5-methyl-3-pyridinecarboxylic acid

2-methoxycarbonyl-5-methyl-3-pyridinecarboxylic acid

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

imazapic
104098-48-8

imazapic

Conditions
ConditionsYield
With sodium methylate at 120℃; for 1h; Temperature;90.8%
pyridine-2,3-dicarboxylic acid 2-methyl ester
24195-07-1

pyridine-2,3-dicarboxylic acid 2-methyl ester

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid
81334-34-1, 81510-77-2, 81510-78-3

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid

Conditions
ConditionsYield
With sodium methylate at 120℃; for 1h; Temperature;90.1%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

C10H11NO4

C10H11NO4

imazapic
104098-48-8

imazapic

Conditions
ConditionsYield
With sodium ethanolate at 110℃; for 1h; Temperature; Reagent/catalyst;89.2%
furo[2,3-b]pyridine-5,6-dicarboxylic anhydride

furo[2,3-b]pyridine-5,6-dicarboxylic anhydride

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid
94746-47-1

6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran88.6%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

C10H11NO4

C10H11NO4

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid
81334-34-1, 81510-77-2, 81510-78-3

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid

Conditions
ConditionsYield
With sodium n-propoxide at 110℃; for 1h;88.5%
pyridine-2,3-dicarboxylic acid-2-butyl ester

pyridine-2,3-dicarboxylic acid-2-butyl ester

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid
81334-34-1, 81510-77-2, 81510-78-3

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid

Conditions
ConditionsYield
With potassium n-butoxide at 110℃; for 1h;88.2%
2-[(ethyloxy)carbonyl]-3-pyridinecarboxylic acid
161522-42-5

2-[(ethyloxy)carbonyl]-3-pyridinecarboxylic acid

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid
81334-34-1, 81510-77-2, 81510-78-3

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid

Conditions
ConditionsYield
With sodium ethanolate at 110℃; for 1h; Temperature; Reagent/catalyst;87.3%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

C12H15NO4

C12H15NO4

imazapic
104098-48-8

imazapic

Conditions
ConditionsYield
With potassium n-butoxide at 120℃; for 1h;87.3%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-bromobenzene-1,3-dicarboxylic acid dichloride
151603-30-4

2-bromobenzene-1,3-dicarboxylic acid dichloride

(+/-)-N,N'-bis(2-carbamoyl-3-methylbut-2-yl)-2-bromobenzene-1,3-dicarboxamide
1276021-20-5

(+/-)-N,N'-bis(2-carbamoyl-3-methylbut-2-yl)-2-bromobenzene-1,3-dicarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 12h;87%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

B

(+)-(R)-2-amino-2,3-dimethylbutanamide
90376-98-0

(+)-(R)-2-amino-2,3-dimethylbutanamide

Conditions
ConditionsYield
In water at 37℃; Ochrobactrum anthropi NCIMB 40321;A 86%
B 74%
With water at 37℃; for 72h; aminopeptidase from Mycobacterium neoaurum ATCC 25795;
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

diethyl 5-ethyl-2,3-pyridinedicarboxylate
105151-39-1

diethyl 5-ethyl-2,3-pyridinedicarboxylate

imazethapyr
81335-77-5

imazethapyr

Conditions
ConditionsYield
With sodium hydride In toluene at 20℃; for 0.25h;85.2%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

benzaldehyde
100-52-7

benzaldehyde

(+/-)-2-N-benzylamino-2,3-dimethylbutanamide
1016561-97-9

(+/-)-2-N-benzylamino-2,3-dimethylbutanamide

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 48h;85%
3-chlorobenzo[b]thiophen-2-carbonyl chloride
21815-91-8

3-chlorobenzo[b]thiophen-2-carbonyl chloride

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

N-(2-carbamoyl-3-methylbut-2-yl)-3-chlorobenzo[b]thiophene-2-carboxamide
1039755-43-5

N-(2-carbamoyl-3-methylbut-2-yl)-3-chlorobenzo[b]thiophene-2-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;85%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

diethyl quinoline-2,3-dicarboxylate
32413-08-4

diethyl quinoline-2,3-dicarboxylate

2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid
81335-37-7

2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid

Conditions
ConditionsYield
With sodium hydride In toluene at 20℃; for 0.25h;83.7%
pentanal
110-62-3

pentanal

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-butyl-4-methyl-4-(2-methylethyl)-imidazolidin-5-one

2-butyl-4-methyl-4-(2-methylethyl)-imidazolidin-5-one

Conditions
ConditionsYield
In methanol; water82%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

N-(1-Carbamoyl-1,2-dimethyl-propyl)-4-chloro-benzamide
40963-06-2

N-(1-Carbamoyl-1,2-dimethyl-propyl)-4-chloro-benzamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;81%
Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;81%
In chloroform Yield given;
2-Picolinic acid

2-Picolinic acid

2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

(+/-)-2-{[2-(aminocarbonyl)-3-methylbut-2-yl]aminocarbonyl}pyridine
898529-74-3

(+/-)-2-{[2-(aminocarbonyl)-3-methylbut-2-yl]aminocarbonyl}pyridine

Conditions
ConditionsYield
Stage #1: 2-Picolinic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran for 0.5h;
Stage #2: 2-amino-2,3-dimethylbutyramide In tetrahydrofuran for 3h;
78%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

(+/-)-N-(2-carbamoyl-3-methylbut-2-yl)-2-bromobenzenecarboxamide
1276021-17-0

(+/-)-N-(2-carbamoyl-3-methylbut-2-yl)-2-bromobenzenecarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 5h;77%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

diethyl 5-ethyl-2,3-pyridinedicarboxylate
105151-39-1

diethyl 5-ethyl-2,3-pyridinedicarboxylate

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]-5-ethyl nicotinic acid

2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]-5-ethyl nicotinic acid

Conditions
ConditionsYield
With sodium methylate In toluene for 1h; Heating;76.5%
With hydrogenchloride; potassium tert-butylate In water; toluene
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-chloro-benzamide

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-chloro-benzamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;75%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-methyl-benzamide

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-methyl-benzamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;75%
2-amino-2,3-dimethylbutyramide
40963-14-2

2-amino-2,3-dimethylbutyramide

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

(+/-)-N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide
100594-41-0, 97712-44-2

(+/-)-N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;70%
With triethylamine In tetrahydrofuran; water
With triethylamine In tetrahydrofuran; water
With triethylamine In acetone
2,3-Dimethylmaleic anhydride
766-39-2

2,3-Dimethylmaleic anhydride

Conditions
ConditionsYield
With sodium ethanolate; triethylamine In ethanol69.9%
2-amino-2,3-dimethylbutyramide

2-amino-2,3-dimethylbutyramide

2,6-difluorobenzoylchloride

2,6-difluorobenzoylchloride

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2,6-difluoro-benzamide

N-(1-Carbamoyl-1,2-dimethyl-propyl)-2,6-difluoro-benzamide

Conditions
ConditionsYield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;68%

40963-14-2Relevant articles and documents

Efficient hydration of 2-amino-2,3-dimethylbutyronitrile to 2-amino-2,3-dimethylbutyramide in a biphasic system via an easily prepared whole-cell biocatalyst

Zhu, Shujing,Ma, Xiaoqiang,Su, Erzheng,Wei, Dongzhi

, p. 3992 - 3999 (2015)

From an environmental perspective, utilizing nonconventional solvents (i.e. green solvents) with low ecological footprints is a highly beneficial alternative to using conventional organic solvents to form a reaction system. The nitrile hydratase (NHase, EC 4.2.1.84) catalyzed hydration of 2-amino-2,3-dimethylbutyronitrile (ADBN) to 2-amino-2,3-dimethylbutyramide (ADBA) in various green solvent-aqueous reaction systems was investigated in this study. After systematically optimizing the reaction conditions, the HFE-7100/H2O (v/v, 10%) biphasic system was ultimately identified as a promising reaction system for reducing product inhibition, avoiding substrate hydrolysis, and facilitating product separation and solvent recovery. The average ADBA yield of an entire batch reaction was 97.3%, which is obviously higher than those obtained with previously reported chemical or enzymatic methods. This is the first attempt to apply a fluorous solvent-aqueous biphasic system to a biocatalytic process, and the results suggest that the fluorous solvent employed in the biphasic system satisfies the requirements for green chemistry.

PREPARATION, 1H AND 13C NMR SPECTRA OF SUBSTITUTED 2-BENZOYLAMINOCARBOXAMIDES

Sedlak, Milos,Halama, Ales,Kavalek, Jaromir,Machacek, Vladimir,Sterba, Vojeslav

, p. 150 - 160 (2007/10/02)

-

Process for the resolution of certain racemic amino nitriles

-

, (2008/06/13)

The invention is a process for the selective and concomitant resolution-racemization-resolution of certain substituted, racemic amino nitriles via their respective tartrate salts. The invention further relates to certain resolved (optically active) amino amides prepared from said amino nitriles, and to the herbicidal substituted oxo-imidazolinyl nicotinic acids and 3-quinoline carboxylic acids prepared therefrom.

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