Phenyl chloroformate → HCID 53934473, compound

HRID 1438855Notes

Reaction equation

HRID 1438855 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][CH3:9])[C:3]=1[C:10]#[N:11].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]>C1(C)C=CC=CC=1>[C:10]([C:3]1[C:4]([S:7][CH2:8][CH3:9])=[N:5][S:6][C:2]=1[NH:1][C:13](=[O:14])[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)#[N:11]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 21399270HCID 21399270, compound

Product 1

HCID 53934473HCID 53934473, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a mixture of 45.0 g of 5-amino-4-cyano-3-(ethylthio)isothiazole and 47.0 g of phenyl chloroformate in 175 ml of dried toluene was heated under reflux for 16 hours; thin-layer chromatography indicated the reaction to be complete. The reaction mixture was cooled to 10°, and the solid collected by filtration to obtain 66.2 of phenyl (4-cyano-3-(ethylthio)-5-isothiazolyl)carbamate, m.p. 223°-225° after recrystallization from acetic acid. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customthe reaction
  4. temperatureThe reaction mixture was cooled to 10°
  5. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-c038e0508a2e4a30b034952d2c915173
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

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