Phenoxycarbonyl isothiocyanate → 3-imino-2-n-propoxycarbonyl-N-phenoxycarbonylthiobutyramide

HRID 437724Notes

Reaction equation

HRID 437724 reaction equation
[NH:1]=[C:2]([CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH2:8][CH3:9])=[O:5].[O:11]([C:18]([N:20]=[C:21]=[S:22])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[NH:1]=[C:2]([CH3:10])[CH:3]([C:4]([O:6][CH2:7][CH2:8][CH3:9])=[O:5])[C:21]([NH:20][C:18]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:19])=[S:22]

Participants

4

Reactant 2

HCID 12212046Phenoxycarbonyl isothiocyanateHCID 21426792n-Propyl 3-iminobutyrate

Product 1

HCID 214268043-imino-2-n-propoxycarbonyl-N-phenoxycarbonylthiobutyramideYield 87.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A warm solution of n-propyl 3-iminobutyrate (18.2 g.) in toluene (75 ml.) was added to a stirred solution of phenoxycarbonyl isothiocyanate (22.8 g.) in toluene (75 ml.). The temperature of the mixture rose from 20° C. to 35° C. The mixture was then stirred for 1.5 hours at the ambient temperature, filtered and the residue washed with light petroleum (b.p. 40°-60° C.) to give 3-imino-2-n-propoxycarbonyl-N-phenoxycarbonylthiobutyramide (36 g.) in the form of an orange solid. This solid was dissolved in ethyl acetate (125 ml.) and treated at 2°-5° C. with a solution of bromine (0.7 ml.) in ethyl acetate (40 ml.) over 15 minutes. The mixture was stirred at the ambient temperature for 1.5 hours and then filtered to give 3-methyl-5-phenoxycarbonylamino-4-n-propoxycarbonylisothiazole hydrobromide (28 g.), m.p. 157°-163° C.

Workup

  1. customrose from 20° C. to 35° C
  2. filtrationfiltered
  3. washthe residue washed with light petroleum (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-ed8f77115c9647ed8f6c9329d8572747
Source dataset
uspto-grants-1977_06
Patent number
US04032323

Reaction notes

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