Thioglycolic Acid → N-Cyclopropyl-3-(2-mercaptoacetamido)-4-methylbenzamide

HRID 1951272Notes

Reaction equation

HRID 1951272 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=O.Cl.[NH2:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:11]([NH:13][CH:14]1[CH2:16][CH2:15]1)=[O:12]>C1(C)C=CC=CC=1>[CH:14]1([NH:13][C:11](=[O:12])[C:10]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:8]([NH:7][C:3](=[O:5])[CH2:2][SH:1])[CH:9]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 1133Thioglycolic Acid2×HCID 442031943-Amino-N-cyclopropyl-4-methylbenzamide hydrochloride

Product 1

HCID 59761419N-Cyclopropyl-3-(2-mercaptoacetamido)-4-methylbenzamideYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of mercaptoacetic acid (1.65 mL, 24.2 mmol) and 5.0 g (22 mmol) of 3-amino-N-cyclopropyl-4-methylbenzamide hydrochloride (prepared as described in WO 04/071440) in toluene (40 mL) was refluxed for 16 h. At this time, an additional 0.8 mL of mercaptoacetic acid was added and the mixture was continued at reflux for an additional 2 days. After cooling to rt, the solid was collected by vacuum filtration and was rinsed with EtOAc (2×50 mL). The resulting solid was then slurried in water (50 mL) and the solid was recollected by vacuum filtration and rinsed with add'n water. The resulting solid was air dried in the funnel then under vacuum overnight to afford 1.86 g (32%) of a white solid as compound a. HPLC Ret time=1.83 min. LCMS [M+H]+ 265.37.

Workup

  1. temperatureat reflux for an additional 2 days
  2. filtrationthe solid was collected by vacuum filtration
  3. washwas rinsed with EtOAc (2×50 mL)
  4. filtrationthe solid was recollected by vacuum filtration
  5. washrinsed with add'n water
  6. customdried in the funnel

Sources & evidence

ORD record
ord-d45f80d89f994a5fa9d26640c0f83629
Source dataset
uspto-grants-2013_03
Patent number
US08404689B2

Reaction notes

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