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

HRID 972523Notes

Reaction equation

HRID 972523 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH2:11])[CH2:4][CH2:3]1.[C:12]([N:20]=[C:21]=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:12]([NH:20][C:21]([NH:11][CH:5]1[C:6]2[CH:10]=[CH:9][S:8][C:7]=2[C:2](=[O:1])[CH2:3][CH2:4]1)=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 233477964-Amino-5,6-dihydro-1-benzothiophen-7(4H)-one

Product 1

HCID 130370141-Benzoyl-3-(4,5,6,7-tetrahydro-7-oxobenzo[b]-thien-4-yl)ureaYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,5,6,7-tetrahydro-7-oxobenzo[b]thiophen-4-amine (8.02 g) in methylene chloride (75 ml) is added to a stirred solution of benzoyl isocyanate (7.0 g) in methylene chloride (75 ml) under a nitrogen atmosphere. The mixture is stirred for an overnight period at room temperature and the title compound is collected by filtration. Recrystallization of the crude product from acetone/hexane affords 5.7 g of the title compound, m.p. 204° to 207° C.

Workup

  1. filtrationthe title compound is collected by filtration
  2. customRecrystallization of the crude product from acetone/hexane

Sources & evidence

ORD record
ord-4045cbfe73d545d29700172d25defd8e
Source dataset
uspto-grants-1977_10
Patent number
US04053484

Reaction notes

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