Ammonia → 4-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxamide

HRID 1459462Notes

Reaction equation

HRID 1459462 reaction equation
C([N:3](CC)CC)C.[NH2:8][C:9]1[C:14]2[CH2:15][CH2:16][O:17][C:13]=2[C:12]([C:18](O)=[O:19])=[CH:11][C:10]=1[Cl:21].ClC(OCC)=O.N>C(Cl)(Cl)Cl>[NH2:8][C:9]1[C:14]2[CH2:15][CH2:16][O:17][C:13]=2[C:12]([C:18]([NH2:3])=[O:19])=[CH:11][C:10]=1[Cl:21]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 106324014-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid

Product 1

HCID 540584804-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxamideYield 69.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.16 mol) was added to a solution of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid (0.16 mol) in chloroform (600 ml) at a temperature below 10° C. Ethyl chloroformate (15.3 ml) was added afterwards and the reaction mixture was stirred for 45 minutes, while cooling on an ice-bath. Gaseous ammonia was allowed to bubble through the mixture and the reaction mixture was stirred for 3 hours at RT. The precipitate was filtered off and consecutively washed with water, 5% NaOH solution, and again water, and dried, yielding 23.5 g (69%) of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxamide (intermediate 7).

Workup

  1. temperaturewhile cooling on an ice-bath
  2. customto bubble through the mixture
  3. stirringthe reaction mixture was stirred for 3 hours at RT
  4. filtrationThe precipitate was filtered off
  5. washconsecutively washed with water, 5% NaOH solution, and again water
  6. customdried

Sources & evidence

ORD record
ord-ab34c0385aa6453e94d06094b8e0e039
Source dataset
uspto-grants-1998_12
Patent number
US05854261

Reaction notes

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