Water → HCID 18769990, compound

HRID 479300Notes

Reaction equation

HRID 479300 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([CH:19]=[CH2:20])=[C:17]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].Cl[C:26](=[N:32][OH:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28].O>ClCCl>[Cl:8][C:9]1[C:18]([CH:19]2[O:33][N:32]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20]2)=[C:17]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 6816376Ethyl chloro(hydroximino)acetate2×HCID 18769993HCID 18769993, compound

Product 1

HCID 18769990HCID 18769990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.4 ml (46 mmol) of triethylamine were added slowly dropwise at room temperature to a solution of 8.5 g (31 mmol) of methyl 2-chloro-3-ethenyl-4-methylsulfonylbenzoate and 7.2 g (46 mmol) of ethyl 2-chloro-2-hydroxyiminoacetate in 200 ml of dichloromethane. After the mixture had been stirred for in each case 2 hours, 3 further portions of in each case 4.8 g (31 mmol) of ethyl 2-chloro-2-hydroxyiminoacetate and then 4.3 ml (31 mmol) of triethylamine were added. Stirring was continued for 12 hours at room temperature, and the reaction mixture was then stirred into 600 ml of water. After extraction with dichloromethane, drying and removal of the solvent, the residue was chromatographed.

Workup

  1. extractionAfter extraction with dichloromethane
  2. customdrying
  3. customremoval of the solvent
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-82a3a564f58f4db6b8ee7ea9fd018e2b
Source dataset
uspto-grants-2003_11
Patent number
US06645919B1

Reaction notes

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