Methyl Isocyanate → N-(7-Methoxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)-N'-methylurea

HRID 1973909Notes

Reaction equation

HRID 1973909 reaction equation
[CH3:1][O:2][CH:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]([NH2:12])[CH2:5][CH2:4]1.[CH3:13][N:14]=[C:15]=[O:16]>CCOCC>[CH3:1][O:2][CH:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]([NH:12][C:15](=[O:16])[NH:14][CH3:13])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 214909534,5,6,7-Tetrahydro-7-methoxybenzo[b]thiophen-4-amine

Product 1

HCID 21490957N-(7-Methoxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)-N'-methylureaYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Crude 4,5,6,7-tetrahydro-7-methoxybenzo[b]thiophen-4-amine (2.3 g, 12.57 mm) is dissolved in ether (50 ml) and the stirred solution treated with a solution of methyl isocyanate (2.9 ml) in ether (10 ml), added over a period of 20 minutes. After stirring overnight the product is filtered off, washed twice with ether (50 ml total) and air dried to afford the title compound (2.25 g, 75% Y) m.p. 152° C-159° C. The analytical sample is recrystallized from acetone and has m.p. 164° C-166° C.

Workup

  1. additionadded over a period of 20 minutes
  2. filtrationis filtered off
  3. washwashed twice with ether (50 ml total) and air
  4. customdried

Sources & evidence

ORD record
ord-ca9fc235187c49958769396e96ff41e0
Source dataset
uspto-grants-1976_12
Patent number
US03998959

Reaction notes

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