Phosgene → N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride

HRID 1248929Notes

Reaction equation

HRID 1248929 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([Cl:18])[C:6]2[O:10][CH:9]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][C:7]=2[CH:17]=1.[C:19](Cl)([Cl:21])=[O:20]>C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([Cl:18])[C:6]2[O:10][CH:9]([CH2:11][N:12]([CH2:13][CH2:14][CH2:15][CH3:16])[C:19]([Cl:21])=[O:20])[CH2:8][C:7]=2[CH:17]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 13563316N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylamine hydrochloride

Product 1

HCID 13563317N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A thoroughly stirred suspension of 26 g (0.0838 mole) of N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylamine hydrochloride in 250 ml of dry ethyl acetate was gassed with phosgene at 50° C. After 4 hours, the suspended material had dissolved. The mixture was evaporated down under reduced pressure, at 50° C. and under 0.5 mbar in the final stage. 27 g of N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride were obtained as a colorless oil, which was reacted further without additional purification.

Workup

  1. dissolutionthe suspended material had dissolved
  2. customThe mixture was evaporated down under reduced pressure, at 50° C. and under 0.5 mbar in the final stage

Sources & evidence

ORD record
ord-23e3c9b01fef4e0eb6c55a989af06c4e
Source dataset
uspto-grants-1986_12
Patent number
US04628058

Reaction notes

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