Triethylamine → N-Methyl-N'-(4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

HRID 259313Notes

Reaction equation

HRID 259313 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.C(N(CC)CC)C.[CH3:19][N:20]=[C:21]=[O:22]>C1C=CC=CC=1>[CH3:19][NH:20][C:21]([NH:11][CH:7]1[C:4]2[CH:5]=[CH:6][S:2][C:3]=2[CH2:10][CH2:9][CH2:8]1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 173886004,5,6,7-Tetrahydrobenzo[b]thiophen-4-amine hydrochloride

Product 1

HCID 20348942N-Methyl-N'-(4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1.89 grams (0.01 mole) of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine hydrochloride in 20 ml. of dry benzene is stirred while 1.05 grams (0.01 mole) of triethylamine and 01.7 ml. (excess) of methyl isocyanate are added successively. Addition of the latter gives rise to an exotherm, and the mixture becomes very pasty. The mixture is kept at 45° C. for 1 hour, and after cooling to room temperature, the solid is collected, washed thoroughly with benzene and then with water. On drying, this gives 1.7 grams (81%) of product, melting point 183° C. to 186° C. Recrystallization from acetone gives 1.23 grams, melting point 187.5° C. to 189° C.

Workup

  1. additionAddition of the latter
  2. customgives rise to an exotherm
  3. customthe solid is collected
  4. washwashed thoroughly with benzene
  5. customOn drying
  6. customRecrystallization from acetone
  7. customgives 1.23 grams, melting point 187.5° C. to 189° C.

Sources & evidence

ORD record
ord-ec8dc9a460f44e558e5199fcbe6e9bc3
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

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