(+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

Base Information

Chemical Name:(+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide
CAS No.:310870-78-1
Molecular Formula:C₁₆H₁₄N₂O₃S
Molecular Weight:314.365
Hs Code.:

Synonyms:(+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

Chemical Property:

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Technology Process of (+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

There total 13 articles about (+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 7677-24-9
trimethylsilyl cyanide

: 310870-77-0
(+/-)-3-hydroxy-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

: 310870-78-1
(+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/jo000952n

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 310870-78-1
(+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

Guidance literature:: Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 4 h / 0 °C

2: 2.73 g / 2N HCl / tetrahydrofuran / 12 h / 25 °C

3: 50 percent / NaIO₄ / RuCl₃(H₂O) / CCl₄; acetonitrile; H₂O / 25 °C

4: 88 percent / DIBALH / CH₂Cl₂ / 1 h / -78 °C

5: 92 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

With hydrogenchloride; sodium periodate; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: Hydrolysis / 3: Oxidation / 4: Reduction / 5: Substitution;
DOI:10.1021/jo000952n

Reference yield:

: 1008-72-6
sodium 2-formylbenzenesulfonate

: 310870-78-1
(+/-)-3-cyano-2-(4-methoxyphenyl)methyl-1,2-benzisothiazoline 1,1-dioxide

Guidance literature:: Multi-step reaction with 11 steps

1.1: K₂CO₃ / H₂O / 6 h / 25 °C

2.1: SOCl₂ / dimethylformamide / 2 h / 80 °C

2.2: 19.5 g / aq. NH₄OH / tetrahydrofuran / 0.17 h / 0 °C

3.1: 86 percent / DIBALH / tetrahydrofuran / 1 h / -78 °C

4.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / powdered 4 Angstroem molecular sieves / CH₂Cl₂; tetrahydrofuran / -20 - -15 °C

5.1: 83 percent / Ti(O-iPr)4; Et₃N / CH₂Cl₂ / 1 h / 25 °C

6.1: 100 percent / PPTS / acetonitrile / 2 h / 25 °C

7.1: NaH / dimethylformamide / 4 h / 0 °C

8.1: 2.73 g / 2N HCl / tetrahydrofuran / 12 h / 25 °C

9.1: 50 percent / NaIO₄ / RuCl₃(H₂O) / CCl₄; acetonitrile; H₂O / 25 °C

10.1: 88 percent / DIBALH / CH₂Cl₂ / 1 h / -78 °C

11.1: 92 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; thionyl chloride; diethyl (2R,3R)-tartrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; ruthenium trichloride; 4 A molecular sieve; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Wittig-Horner-Emmons reaction / 1.2: transesterification / 2.1: Substitution / 2.2: Substitution / 3.1: Reduction / 4.1: Epoxidation / 5.1: Cyclization / 6.1: Cyclization / 7.1: Alkylation / 8.1: Hydrolysis / 9.1: Oxidation / 10.1: Reduction / 11.1: Substitution;
DOI:10.1021/jo000952n