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

HRID 1730988Notes

Reaction equation

HRID 1730988 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([N:11]=[C:12]=[O:13])[CH2:4][CH2:3]1.Cl.[CH3:15][O:16][NH2:17].C(N(CC)CC)C>CCOCC>[CH3:15][O:16][NH:17][C:12]([NH:11][CH:5]1[C:6]2[CH:10]=[CH:9][S:8][C:7]=2[C:2](=[O:1])[CH2:3][CH2:4]1)=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 203489024-Isocyanato-5,6-dihydro-1-benzothiophen-7(4H)-one

Product 1

HCID 21316219N-Methoxy-N'-(7-oxo-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The crude ether solution of 4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl isocyanate prepared in Example 4 is added dropwise to a mixture of methoxyamine hydrochloride (9.02 g), triethylamine (13.67 g) and ether (50 ml) under a nitrogen atmosphere. After stirring for 36 hours at room temperature, the solid in the reaction mixture is collected and washed with water. The water-insoluble solid is recrystallized twice from acetone-hexane to afford the title urea, m.p. 185° to 188.5° C.

Workup

  1. customthe solid in the reaction mixture is collected
  2. washwashed with water
  3. customThe water-insoluble solid is recrystallized twice from acetone-hexane

Sources & evidence

ORD record
ord-a2c28e5048a74baf80a1fd023f5adf6d
Source dataset
uspto-grants-1976_11
Patent number
US03994924

Reaction notes

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