Benzoyl isocyanate → 1-Benzoyl-3-(4,5,6,7-tetrahydrobenzo-[b]thien-4-yl)urea

HRID 1155644Notes

Reaction equation

HRID 1155644 reaction equation
[C:1]([N:9]=[C:10]=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12]1[CH:16]=[CH:15][C:14]2[CH:17]([NH2:21])[CH2:18][CH2:19][CH2:20][C:13]1=2>C(Cl)Cl>[C:1]([NH:9][C:10]([NH:21][CH:17]1[C:14]2[CH:15]=[CH:16][S:12][C:13]=2[CH2:20][CH2:19][CH2:18]1)=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 42163724,5,6,7-Tetrahydro-1-benzothiophen-4-amine

Product 1

HCID 130370061-Benzoyl-3-(4,5,6,7-tetrahydrobenzo-[b]thien-4-yl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2.94 g sample of benzoyl isocyanate in 5 ml of CH2Cl2 is added to 3.04 g of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine in 50 ml of CH2Cl2 under N2 atmosphere. After stirring overnight at room temperature, the reaction mixture is evaporated to dryness in vacuo. The residue is then stirred in 100 ml of Et2O and filtered to afford 1-benzoyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)urea, m.p. 189° C. to 194° C. Substitution of trichloroacetyl isocyanate for benzoyl isocyanate affords 1-trichloroacetyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)urea. Use of 4,5,6,7-tetrahydrobenzo[b]thien-4-ylisocyanate and acetamide in the above manner affords 1-acetyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)urea.

Workup

  1. customthe reaction mixture is evaporated to dryness in vacuo
  2. stirringThe residue is then stirred in 100 ml of Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-469e131d73d54d6d90025cb5fad53904
Source dataset
uspto-grants-1982_06
Patent number
US04332724

Reaction notes

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