4-Bromophenyl isocyanate → HCID 12405739, compound

HRID 436817Notes

Reaction equation

HRID 436817 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][C:12]1[S:13][C:14]2[C:20]([Cl:21])=[C:19]([Cl:22])[CH:18]=[C:17]([S:23][C:24]#[N:25])[C:15]=2[N:16]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:11][C:12]2[S:13][C:14]3[C:20]([Cl:21])=[C:19]([Cl:22])[CH:18]=[C:17]([S:23][C:24]#[N:25])[C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 756094-Bromophenyl isocyanateHCID 124057332-Amino-6,7-dichloro-4-thiocyanatobenzothiazole

Product 1

HCID 12405739HCID 12405739, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Bromophenyl isocyanate (20 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 300 ml. of dimethylformamide. The solution was heated at 100° with stirring for 41/2 hours and cooled at 0° overnight. The solid was collected by filtration. The filtrate was poured into ice water and the solid was collected by filtration. The combined solids were recrystallized from a methanol-dimethylformamide-water mixture to give 22 g. (50%) of product. Recrystallization from ethanol gave an analytical sample, m.p. 243°-245° .

Workup

  1. temperatureThe solution was heated at 100°
  2. temperaturecooled at 0° overnight
  3. filtrationThe solid was collected by filtration
  4. additionThe filtrate was poured into ice water
  5. filtrationthe solid was collected by filtration
  6. customThe combined solids were recrystallized from a methanol-dimethylformamide-water mixture
  7. customto give 22 g
  8. customRecrystallization from ethanol
  9. customgave an analytical sample, m.p. 243°-245°

Sources & evidence

ORD record
ord-3f351fbb63ab4fe2bac40b7d5f867dfa
Source dataset
uspto-grants-1977_06
Patent number
US04028374

Reaction notes

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