N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine

Base Information

• Chemical Name: N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine
• CAS No.: 132169-38-1
• Molecular Formula: C₂₄H₂₇BrN₂OS
• Molecular Weight: 471.461
• Mol file: 132169-38-1.mol

Synonyms:

Chemical Property of N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine

There total 11 articles about N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine 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:

2-bromo-3-nitro-benzoic acid (573-54-6) → N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine (132169-38-1)

Guidance literature:

Multi-step reaction with 10 steps

1: BH₃*THF / tetrahydrofuran / 0 deg C, 1 h; r.t., 3 h

2: Fe, HCl / acetic acid; ethanol / 3 h / Heating

3: imidazole, DMAP / dimethylformamide / 18 h / Ambient temperature

4: 91 percent / LDA / tetrahydrofuran / -78 deg C, 30 min; r.t., 4 h

5: tetrahydrofuran / 3 h / Ambient temperature

6: HF / acetonitrile / Ambient temperature

7: 98 percent / PCC, SiO₂, DCM / 6 h / Ambient temperature; ultrasound

8: 1.) HMDSLi / 1.) THF, -78 deg C -> 0 deg C, 90 min; 2.) THF, r.t., 24 h

9: 89 percent / 10percent HCl / tetrahydrofuran / 24 h

10: 91 percent / molecular sieves / toluene / 4 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; dmap; molecular sieve; borane-THF; hydrogen fluoride; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; silica gel; iron; pyridinium chlorochromate; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; ethanol; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)85078-X

Reference yield:

2-bromo-(3-tert-butyldimethylsilyloxymethyl)aniline (132169-30-3) → N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine (132169-38-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / LDA / tetrahydrofuran / -78 deg C, 30 min; r.t., 4 h

2: tetrahydrofuran / 3 h / Ambient temperature

3: HF / acetonitrile / Ambient temperature

4: 98 percent / PCC, SiO₂, DCM / 6 h / Ambient temperature; ultrasound

5: 1.) HMDSLi / 1.) THF, -78 deg C -> 0 deg C, 90 min; 2.) THF, r.t., 24 h

6: 89 percent / 10percent HCl / tetrahydrofuran / 24 h

7: 91 percent / molecular sieves / toluene / 4 h / Ambient temperature

With hydrogenchloride; molecular sieve; hydrogen fluoride; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; silica gel; pyridinium chlorochromate; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)85078-X

Reference yield:

3-(N-acetyl-N-allylamino)-2-bromobenzyl alcohol (132169-31-4) → N-2-<3-(N-acetyl-N-allylamino)-2-bromophenyl>ethenyl-2-(phenythiomethyl)prop-2-enylmethylamine (132169-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / PCC, SiO₂, DCM / 6 h / Ambient temperature; ultrasound

2: 1.) HMDSLi / 1.) THF, -78 deg C -> 0 deg C, 90 min; 2.) THF, r.t., 24 h

3: 89 percent / 10percent HCl / tetrahydrofuran / 24 h

4: 91 percent / molecular sieves / toluene / 4 h / Ambient temperature

With hydrogenchloride; molecular sieve; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; silica gel; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4020(01)85078-X

upstream raw materials:

2-bromo-3-nitro-benzoic acid

2-bromo-3-(hydroxymethyl)-1-nitrobenzene

2-bromo-(3-tert-butyldimethylsilyloxymethyl)aniline

3-(N-acetyl-N-allylamino)-2-bromobenzaldehyde