Hexane → (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-prop-2-enoxyiminoacetyl chloride;hydrochloride

HRID 465258Notes

Reaction equation

HRID 465258 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:15]/[O:16][CH2:17][CH:18]=[CH2:19])/[C:12](O)=[O:13])[N:10]=1)=[O:4].P(Cl)(Cl)(Cl)(Cl)[Cl:21].CCCCCC>C(Cl)Cl>[ClH:1].[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:15]/[O:16][CH2:17][CH:18]=[CH2:19])/[C:12]([Cl:21])=[O:13])[N:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 8058HexaneHCID 24819Phosphorus pentachlorideHCID 14230763(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-prop-2-enoxyiminoacetic acid

Product 1

HCID 21244940(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-prop-2-enoxyiminoacetyl chloride;hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 13 ml of methylene chloride is suspended 610 mg of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-allyloxyiminoacetic acid and under ice-cooling and stirring 502.4 mg of phosphorus pentachloride is added. The mixture is stirred at room temperature for 30 minutes, after which 100 ml of hexane is added to the reaction mixture. The resulting crystals are recovered by filtration and washed with hexane to give 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-allyloxyiminoacetyl chloride hydrochloride, m.p. 67°-70° C.

Workup

  1. temperatureunder ice-cooling
  2. additionis added
  3. filtrationThe resulting crystals are recovered by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-083c9b81bbac4e7a812b4d005cfccb48
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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