Thiophosgene → (4-Chloro-3-isothiocyanatophenyl)phenylmethanone

HRID 1902622Notes

Reaction equation

HRID 1902622 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17](Cl)(Cl)=[S:18]>O1CCOCC1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:3][C:2]=1[N:1]=[C:17]=[S:18]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 107995483-amino-4-chlorobenzophenone

Product 1

HCID 12874009(4-Chloro-3-isothiocyanatophenyl)phenylmethanoneYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 17 parts of (3-amino-4-chlorophenyl) phenylmethanone, 9.5 parts of carbonothioic dichloride and 200 parts of 1,4-dioxane is stirred and refluxed for 15 minutes. The reaction mixture is evaporated and the oily residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 17 parts (85%) of (4-chloro-3-isothiocyanatophenyl)phenylmethanone; mp. 96.7° C.

Workup

  1. temperaturerefluxed for 15 minutes
  2. customThe reaction mixture is evaporated
  3. customthe oily residue is crystallized from 2,2'-oxybispropane
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-f27cd6de6a914db9b8fe4c73eceab209
Source dataset
uspto-grants-1982_12
Patent number
US04364942

Reaction notes

Loading…