Phenyl chloroformate → HCID 23361835, compound

HRID 1506130Notes

Reaction equation

HRID 1506130 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[S:4][N:3]=1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:9](=[O:10])[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:4][N:3]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 323073-Methylisothiazol-5-amine

Product 1

HCID 23361835HCID 23361835, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methylisothiazol-5-amine (156 mg, 1.04 mmol) in pyridine (1.2 mL) was mixed with phenyl chloroformate (260 μL, 2.07 mmol) under cooling with ice and stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and after addition of water, extracted with chloroform twice, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a pale yellow solid (173 mg, yield 71%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionafter addition of water
  4. extractionextracted with chloroform twice
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-af974ce0027943b0af06a157e9426cf5
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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