Dimethylformamide → HCID 22818692, compound

HRID 1277904Notes

Reaction equation

HRID 1277904 reaction equation
CN(C)C=O.S(Cl)([Cl:8])=O.[CH3:10][C:11]1([CH3:23])[C@@H:13]([CH:14]([Br:19])[C:15]([Br:18])([Br:17])[Br:16])[C@H:12]1[C:20](O)=[O:21]>C(Cl)Cl>[CH3:10][C:11]1([CH3:23])[C@@H:13]([CH:14]([Br:19])[C:15]([Br:18])([Br:17])[Br:16])[C@H:12]1[C:20]([Cl:8])=[O:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 12874364HCID 12874364, compound

Product 1

HCID 22818692HCID 22818692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.2 ml of dimethylformamide, 8.5 ml of thionyl chloride and 179 ml of petroleum ether (b.p.=35°-75° C.) was heated to reflux and a mixture of 35.76 g of the product of Step A in 150 ml of methylene chloride was added thereto. The mixture was refluxed with stirring for 2 hours and was then cooled and evaporated to dryness. The residue was taken up in toluene and the mixture was evaporated to dryness under reduced pressure to obtain 38 g of raw (1R,cis) 2,2-dimethyl-3-(1',2',2',2'-tetrabromoethyl)-cyclopropane-1-carboxylic acid chloride with a melting point of 88° C. which was used as is for the next step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. additionwas added
  4. temperatureThe mixture was refluxed
  5. temperaturewas then cooled
  6. customevaporated to dryness
  7. customthe mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-febd3f9739a54d51b84a0b8f6ec83389
Source dataset
uspto-grants-1981_07
Patent number
US04279835

Reaction notes

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