Isocyanate → HCID 13229720, compound

HRID 615205Notes

Reaction equation

HRID 615205 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]([Cl:29])([Cl:28])[S:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1.[N-]=C=O>C(Cl)Cl>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([NH:6][C:7]([N:17]([S:16][C:15]([Cl:29])([Cl:14])[Cl:28])[C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=1)=[O:8])=[O:5]

Participants

5

Reactant 3

HCID 105034IsocyanateHCID 27333692,6-Difluorobenzoyl isocyanateHCID 20429530N-[(Trichloromethyl)sulfanyl]-4-(trifluoromethyl)aniline

Product 1

HCID 13229720HCID 13229720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.0 g of 2,6-difluorobenzoyl isocyanate in 15 ml of dry methylene chloride was added to a stirred solution of 3.1 g of 1,1,1-trichloro-N-[4-(trifluoromethyl)phenyl]methanesulphenamide in 35 ml of the same solvent at room temperature. After 2 days, only partial reaction had occurred and 2.0 g of the isocyanate was added. After a total reaction time of 28 days, the reaction mixture was diluted with 400 ml of light petroleum (b.p. 40°-60° C.) and filtered. Evaporation of the solvent from the filtrate gave a residue from which 6 was obtained as colorless crystals, m.p.: 129°-130° C., by chromatography on silica gel using methylene chloride as eluent.

Workup

  1. customonly partial reaction
  2. filtrationfiltered
  3. customEvaporation of the solvent from the filtrate
  4. customgave a residue from which 6
  5. customwas obtained as colorless crystals, m.p.: 129°-130° C., by chromatography on silica gel

Sources & evidence

ORD record
ord-1f731271693c41888ede87b79b3a5d3d
Source dataset
uspto-grants-1985_02
Patent number
US04497822

Reaction notes

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