3-Aminobenzamide → HCID 374038, compound

HRID 862414Notes

Reaction equation

HRID 862414 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH2:14])=[O:13]>C(O)=O>[CH:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH2:14])=[O:13])=[O:3]

Participants

4

Reactant 2

HCID 16453-Aminobenzamide2×HCID 7918Acetic Anhydride

Product 1

HCID 374038HCID 374038, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 40 ml of acetic anhydride and 40 ml of 98 to 100% formic acid was heated at 50° to 60° C. for 90 minutes. The solution was cooled to room temperature and 10 gm of 3-aminobenzamide was added in small aliquots over 15 minutes. The temperature was kept below 30° C. by occasional cooling in an ice-bath during the addition of the 3-aminobenzamide. The solution was stirred at room temperature for 2.5 hours, and then it was evaporated under vacuum to a viscous oil. Traces of acetic anhydride and of formic acid were removed by the repeated addition of water and evaporation until a white solid product was obtained. The solid product was crystallized from water. The white, round crystals were filtered off and washed with cold water and then dried under a vacuum. The overall yield was 78% and the melting point of the final material was 175° C. to 177° C. Mass spectrum analysis indicated a molecular weight of 164.

Workup

  1. temperaturewas heated at 50° to 60° C. for 90 minutes
  2. customwas kept below 30° C.
  3. customit was evaporated under vacuum to a viscous oil
  4. customTraces of acetic anhydride and of formic acid were removed by the repeated addition of water and evaporation until a white solid product
  5. customwas obtained
  6. customThe solid product was crystallized from water
  7. filtrationThe white, round crystals were filtered off
  8. washwashed with cold water
  9. customdried under a vacuum
  10. customwas 175° C. to 177° C

Sources & evidence

ORD record
ord-9675677aef584b67b7ae98e92f8724ce
Source dataset
uspto-grants-1998_02
Patent number
US05719151

Reaction notes

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