Thionyl Chloride → 4-Amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride

HRID 362784Notes

Reaction equation

HRID 362784 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11](O)=[O:12])=[CH:4][C:3]=1[Cl:14].S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([Cl:17])=[O:12])=[CH:4][C:3]=1[Cl:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 106324014-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid

Product 1

HCID 539800704-Amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid (4.3 g) in thionyl chloride (100 ml) and CHCl3 (200 ml) was stirred and refluxed for 2 hours. The mixture was cooled and the solvent was evaporated. Toluene was added and evaporated again, yielding 4.8 g of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride (100% crude residue) (intermediate 7).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated
  4. additionToluene was added
  5. customevaporated again

Sources & evidence

ORD record
ord-1043e9bb59bb4746884d7d3f2f8ad2eb
Source dataset
uspto-grants-1999_02
Patent number
US05872131

Reaction notes

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