Hexane → HCID 22166461, compound

HRID 653307Notes

Reaction equation

HRID 653307 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][C:17]([CH3:32])([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[CH3:18])/[C:12](O)=[O:13])[N:10]=1)=[O:4].P(Cl)(Cl)(Cl)(Cl)[Cl:34].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][C:17]([CH3:32])([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[O:20])[CH3:18])/[C:12]([Cl:34])=[O:13])[N:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 8058HexaneHCID 24819Phosphorus pentachlorideHCID 14038627HCID 14038627, compound

Product 1

HCID 22166461HCID 22166461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 15 ml of methylene chloride is dissolved 1.445 g of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid and under ice-cooling and stirring 686 mg of phosphorus pentachloride is added. The mixture is stirred under ice-cooling for 30 minutes, after which 4.5 ml of hexane is added. The resultant crystalline precipitate is collected by filtration and washed with hexane to give 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)-ethyloxyimino]acetyl chloride hydrochloride, m.p. 79°-82° C.

Workup

  1. temperatureunder ice-cooling
  2. additionis added
  3. temperaturecooling for 30 minutes
  4. filtrationThe resultant crystalline precipitate is collected by filtration
  5. washwashed with hexane

Sources & evidence

ORD record
ord-7aa77d02ec5c404dac561879a4af8e2b
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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