Phenoxycarbonyl isothiocyanate → 2-ethoxycarbonyl-3-imino-N-phenoxycarbonylthiohexanamide

HRID 437731Notes

Reaction equation

HRID 437731 reaction equation
[NH:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O:12]([C:19]([N:21]=[C:22]=[S:23])=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:7]([O:6][C:4]([CH:3]([C:2](=[NH:1])[CH2:9][CH2:10][CH3:11])[C:22]([NH:21][C:19]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:20])=[S:23])=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 12212046Phenoxycarbonyl isothiocyanateHCID 21426807Ethyl 3-iminohexanoate

Product 1

HCID 538115052-ethoxycarbonyl-3-imino-N-phenoxycarbonylthiohexanamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of ethyl 3-iminohexanoate (31.4 g.) in toluene (25 ml.) was added to a stirred solution of phenoxycarbonyl isothiocyanate (36 g.) in toluene (75 ml.) at 20° C. The temperature rose to 54° C. The mixture was allowed to cool to room temperature, filtered, and the solid washed with light petroleum (b.p. 40°-60° C.) to give 2-ethoxycarbonyl-3-imino-N-phenoxycarbonylthiohexanamide (62 g.) in the form of a yellow powder. This powder was suspended in ethyl acetate (150 ml.) and treated at 0°-5° C. with a solution of bromine (10.5 ml.) in ethyl acetate (50 ml.) during 20 minutes. The mixture was stirred for a further hour and then filtered, and the solid washed with light petroleum (b.p. 40°-60° C.) to give 4-ethoxycarbonyl-5-phenoxycarbonylamino-3-n-propylisothiazole hydrobromide (69 g.) m.p. 135°-138° C.

Workup

  1. customrose to 54° C
  2. filtrationfiltered
  3. washthe solid washed with light petroleum (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-f18728dd10ca4dc98a9c7433ef0ce2db
Source dataset
uspto-grants-1977_06
Patent number
US04032323

Reaction notes

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