2-Propanone, 1-(acetyloxy)-3-chloro- → HCID 67025539, compound

HRID 2390553Notes

Reaction equation

HRID 2390553 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:9]([O:12][CH2:13][C:14](=O)[CH2:15]Cl)(=[O:11])[CH3:10]>C1(C)C=CC=CC=1>[C:9]([O:12][CH2:13][C:14]1[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][CH:15]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 2733398Ethyl thiooxamate

Product 1

HCID 67025539HCID 67025539, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-amino-2-thioxoacetate (0.5 g, 3.75 mmol) and 3-chloro-2-oxopropyl acetate (0.565 g, 3.75 mmol) were dissolved in toluene (10 mL) and heated in a microwave at 100° C. for 1 h then heated for a further 3 h at 120° C. Cooled to RT, evaporated in vacuo and purified by chromatography on silica with 20% EtOAc/isohexane as eluent to afford the sub-title compound as a pale yellow solid. Yield: 0.7 g

Workup

  1. temperaturethen heated for a further 3 h at 120° C
  2. temperatureCooled to RT
  3. customevaporated in vacuo
  4. custompurified by chromatography on silica with 20% EtOAc/isohexane as eluent

Sources & evidence

ORD record
ord-dc80004f148d41519a468b6c394d8b20
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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