Thioglycolic Acid → 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide

HRID 1184824Notes

Reaction equation

HRID 1184824 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:22])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:20]#[N:21])([CH3:19])[CH3:18])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[SH:23][CH2:24][C:25](O)=[O:26]>>[C:20]([C:17]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:10]([NH:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([NH:1][C:25](=[O:26])[CH2:24][SH:23])[CH:3]=1)=[O:22])([CH3:19])[CH3:18])#[N:21]

Participants

3

Reactant 2

HCID 1133Thioglycolic AcidHCID 67125542N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide

Product 1

HCID 866801643-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamideYield 80%

Procedure

A solution of N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (500 mg, 1.704 mmol) in mercaptoacetic acid (3 mL, 43.2 mmol) was stirred at 100° C. for 2 h. Quenched with water and extracted with EtOAc. Organic layer was washed with NaHCO3 solution, brine, dried and evaporated. Purification by chromatography (0-4% methanol in CH2Cl2) gave pure 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide 16 (500 mg, 80%). 1H-NMR (400 MHz, CDCl3) 1.78 (s, 6H), 2.31 (s, 3H), 3.45 (d, J=9.4 Hz, 2H), 7.21 (d, J=8.2 Hz, 1H), 7.52 (t, J=8.2 Hz, 1H), 7.70-7.79 (m, 3H), 7.92-8.08 (m, 3H), 8.67 (br s, 1H).

Workup

  1. customQuenched with water
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with NaHCO3 solution, brine
  4. customdried
  5. customevaporated
  6. customPurification by chromatography (0-4% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-233ca4e9406a4cc28d2b7a38d7b39369
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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