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

HRID 259330Notes

Reaction equation

HRID 259330 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([NH2:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.Cl.[O-:12][C:13]#[N:14].[K+]>O>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([NH:10][C:13]([NH2:14])=[O:12])[CH2:7][CH2:8][CH2:9][C:2]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 42163724,5,6,7-Tetrahydro-1-benzothiophen-4-amineHCID 11378442Potassium cyanate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A sample of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine (19.9 grams) is cooled in a flask, and a solution of 12 ml. of 12N hydrochloric acid in 50 ml. of water is slowly added. Subsequently, at about 20° C., a solution of 11.7 grams of potassium cyanate in 80 ml. of water is added in 0.5 hour. The mixture is stirred at room temperature for one hour and then warmed to 60° C. and kept at this temperature for 0.5 hour. After standing overnight at room temperature, the product is collected and washed with water to afford 21 grams, melting point 206° C. to 209° C.

Workup

  1. customat about 20° C.
  2. temperaturewarmed to 60° C.
  3. waitkept at this temperature for 0.5 hour
  4. waitAfter standing overnight at room temperature
  5. customthe product is collected
  6. washwashed with water
  7. customto afford 21 grams, melting point 206° C. to 209° C.

Sources & evidence

ORD record
ord-a83ba7cfc42f45ab9be136900302dc0e
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

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