Diethylformamide → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride

HRID 1763714Notes

Reaction equation

HRID 1763714 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14](O)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.S(Cl)([Cl:24])=O.C(N(CC)C=O)C>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14]([Cl:24])=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

5

Reactant 3

HCID 12051DiethylformamideHCID 24386Thionyl ChlorideHCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

Product 1

HCID 203106912-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.0 G. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid is dissolved in 25 ml. of chloroform, and 1 ml. of thionyl chloride and 0.1 ml. of diethylformamide are added thereto. The mixture is left for 1 hour then evaporated under high vacuum to afford 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride. In similar manner, substituting the acids prepared in Preparations 3 and 5-8 for the 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid used above, the corresponding acid chlorides are prepared.

Workup

  1. customthen evaporated under high vacuum

Sources & evidence

ORD record
ord-37aa3d6738f6450882ca7f454f723e28
Source dataset
uspto-grants-1978_09
Patent number
US04112114

Reaction notes

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