3,4-Dichlorophenyl isocyanate → HCID 12405740, compound

HRID 436818Notes

Reaction equation

HRID 436818 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:12][C:13]1[S:14][C:15]2[C:21]([Cl:22])=[C:20]([Cl:23])[CH:19]=[C:18]([S:24][C:25]#[N:26])[C:16]=2[N:17]=1>CN(C)C=O>[Cl:23][C:20]1[CH:19]=[C:18]([S:24][C:25]#[N:26])[C:16]2[N:17]=[C:13]([NH:12][C:10]([NH:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[O:11])[S:14][C:15]=2[C:21]=1[Cl:22]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 124057332-Amino-6,7-dichloro-4-thiocyanatobenzothiazole

Product 1

HCID 12405740HCID 12405740, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dichlorophenyl isocyanate (18.8 g., 0.10 mole) was added in portions to a solution of 27.6 g. (0.10 mole) of 2-amino-6,7-dichloro-4-thiocyanatobenzothiazole in 200 ml. of dimethylformamide. The solution was heated at 110° for 5 hours with stirring and cooled at 0° overnight. The solid was collected by filtration to give 28 g. (60%) of product. Two recrystallizations from ethanol gave 13 g. (28%) of analytical material, m.p. 313°-320° (dec.).

Workup

  1. temperatureThe solution was heated at 110° for 5 hours
  2. temperaturecooled at 0° overnight
  3. filtrationThe solid was collected by filtration
  4. customto give 28 g
  5. customTwo recrystallizations from ethanol
  6. customgave 13 g

Sources & evidence

ORD record
ord-8ec4b0737b4943949ba367fd4e3fd76d
Source dataset
uspto-grants-1977_06
Patent number
US04028374

Reaction notes

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