2-Chlorobenzoyl isocyanate → HCID 20397101, compound

HRID 462699Notes

Reaction equation

HRID 462699 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[F:13][C:14]([F:37])([F:36])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23][C:24]2[CH:35]=[CH:34][CH:33]=[CH:32][C:25]=2[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([NH:6][C:7]([N:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:14]([F:13])([F:36])[F:37])=[CH:21][CH:20]=1)[S:23][C:24]1[CH:35]=[CH:34][CH:33]=[CH:32][C:25]=1[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 99423112-Chlorobenzoyl isocyanateHCID 20397095HCID 20397095, compound

Product 1

HCID 20397101HCID 20397101, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 2-chlorobenzoyl isocyanate (2.7 g) in dry toluene (5.0 ml) was added to a stirred suspension of isopropyl 2-[[[4-(trifluoromethoxy)phenyl]amino]thio]benzoate (3.7 g) in the same solvent (20.0 ml) at room temperature. After 18 hours, a cake of crystals had formed. The reaction mixture was cooled to -5° C. and filtered, washing the crystals with cold toluene followed by light petroleum. After drying at 40° C. under vacuum, the pure product was obtained as colourless crystals (4.8 g). Melting point 143°-144° C.

Workup

  1. customa cake of crystals had formed
  2. filtrationfiltered
  3. washwashing the crystals with cold toluene
  4. customAfter drying at 40° C. under vacuum

Sources & evidence

ORD record
ord-701f5fcd385f473d8a457969f53416db
Source dataset
uspto-grants-1985_05
Patent number
US04517193

Reaction notes

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