Urea → N-(4,5,6,7-Tetrahydro-1-benzothiophen-4-yl)urea

HRID 263211Notes

Reaction equation

HRID 263211 reaction equation
O[CH:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.ClC1C2C=CSC=2CCC1.[NH2:21][C:22]([NH2:24])=[O:23]>S(Cl)(Cl)=O.CN(C)C=O.C(N(C(C)C)CC)(C)C>[S:7]1[CH:8]=[CH:9][C:10]2[CH:2]([NH:21][C:22]([NH2:24])=[O:23])[CH2:3][CH2:4][CH2:5][C:6]1=2

Participants

7

Reactant 3

HCID 1176UreaHCID 139116314-Hydroxy-4,5,6,7-tetrahydrobenzo[b]thiopheneHCID 203489224-Chloro-4,5,6,7-tetrahydrobenzo[b]thiophene

Product 1

HCID 13036998N-(4,5,6,7-Tetrahydro-1-benzothiophen-4-yl)urea

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 24386Thionyl ChlorideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A 1 gram sample of 4-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene is stirred in the cold for several hours in thionyl chloride (5 ml.) and the mixture is evaporated to dryness. The crude 4-chloro-4,5,6,7-tetrahydrobenzo[b]thiophene is then added to a mixture of urea (1-5 mole-equivalents) in dimethylformamide and diisopropyl ethylamine. The mixture is warmed, after several hours, to 50° C. and after 4 hours is poured on ice and the product, 4,5,6,7-tetrahydrobenzo[b]thien-4-ylurea, is collected by filtration.

Workup

  1. customthe mixture is evaporated to dryness
  2. additionis poured on ice
  3. filtrationthe product, 4,5,6,7-tetrahydrobenzo[b]thien-4-ylurea, is collected by filtration

Sources & evidence

ORD record
ord-fa99fafdac9143eaad5a0de2ff22cd4a
Source dataset
uspto-grants-1979_05
Patent number
US04156670

Reaction notes

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