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

HRID 263186Notes

Reaction equation

HRID 263186 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:11])[CH2:8][CH2:9][CH2:10][C:3]1=2.[O-:12][C:13]#[N:14].[K+]>O>[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH:11][C:13]([NH2:14])=[O:12])[CH2:8][CH2:9][CH2:10][C:3]1=2

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 173886004,5,6,7-Tetrahydrobenzo[b]thiophen-4-amine hydrochloride

Product 1

HCID 13036998N-(4,5,6,7-Tetrahydro-1-benzothiophen-4-yl)ureaYield 22.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 50 grams of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine hydrochloride (about 45 grams real, based on 90% purity) in 100 ml. of water is stirred at about 15° C., and a solution of 23.1 grams of potassium cyanate in 100 ml. of water is added dropwise. After completion of the addition, the mixture is warmed slowly to 70° C. to 75° C. and held for an hour. The mixture is cooled, and the white solid is collected by filtration and washed with water. The solid is air-dried, pulverized, and washed with acetonitrile. On drying, this gives 37.3 grams of crude product, which on treatment with about 1200 ml. of hot acetone gives 11.45 grams, melting point 200° C. to 204° C. of the title compound.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture is warmed slowly to 70° C. to 75° C.
  3. waitheld for an hour
  4. temperatureThe mixture is cooled
  5. filtrationthe white solid is collected by filtration
  6. washwashed with water
  7. customThe solid is air-dried
  8. washwashed with acetonitrile
  9. customOn drying

Sources & evidence

ORD record
ord-5cc89ae9f10c461690698140f53193f9
Source dataset
uspto-grants-1979_05
Patent number
US04156670

Reaction notes

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