Trichloroacetyl isocyanate → HCID 70196762, compound

HRID 342464Notes

Reaction equation

HRID 342464 reaction equation
Cl.[NH2:2][C:3]1[CH:13]=[C:12]([NH:14][C:15](=[O:24])[C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[C:6]2[O:7][C:8]([CH3:11])=[C:9]([CH3:10])[C:5]=2[CH:4]=1.ClC(Cl)(Cl)[C:27]([N:29]=C=O)=[O:28]>C(N(CC)CC)C>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[C:15]([NH:14][C:12]1[C:6]2[O:7][C:8]([CH3:11])=[C:9]([CH3:10])[C:5]=2[CH:4]=[C:3]([NH:2][C:27]([NH2:29])=[O:28])[CH:13]=1)=[O:24]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 70200669HCID 70200669, compound

Product 1

HCID 70196762HCID 70196762, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5-amino-7-(2,6-dichlorobenzoylamino)-2,3-dimethylbenzo[b]furan hydrochloride (155 mg), triethylamine (61 mg) and trichloroacetyl isocyanate (115 mg) was stirred at ambient temperature for 1 hour. Then, the mixture was concentrated in vacuo and to the residue was added methanol (3 ml) and aqueous 1N-sodium hydroxide (2 ml). The mixture was stirred at 60° C. for 15 minutes and the methanol was evaporated in vacuo. The separated solid was collected, washed with water and dried to give 7-(2,6-dichlorobenzoylamino)-2,3-dimethyl-5-ureidobenzo[b]furan (130 mg).

Workup

  1. concentrationThen, the mixture was concentrated in vacuo and to the residue
  2. additionwas added methanol (3 ml) and aqueous 1N-sodium hydroxide (2 ml)
  3. stirringThe mixture was stirred at 60° C. for 15 minutes
  4. customthe methanol was evaporated in vacuo
  5. customThe separated solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-28cf31e010d548da8d6a01040759604e
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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