Chloroacetyl chloride → methyl (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetate

HRID 621040Notes

Reaction equation

HRID 621040 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[C:4](/[C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)=[N:5]\[O:6][CH2:7][CH2:8][CH3:9].[Cl:17][CH2:18][C:19](Cl)=[O:20]>>[CH3:1][O:2][C:3](=[O:16])/[C:4](/[C:10]1[N:11]=[C:12]([NH:15][C:19](=[O:20])[CH2:18][Cl:17])[S:13][CH:14]=1)=[N:5]\[O:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 14230751methyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetate

Product 1

HCID 14230755methyl (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetateYield 96.7%

Procedure

To a solution of 5.0 g of 2-(2-amino-4-thiazolyl)-(Z)-2-(n-propoxyimino)acetic acid methyl ester in 35 ml of N,N-dimethylacetamido is added dropwise under ice-cooling and stirring 3.25 g of chloroacetyl chloride in the course of 10 minutes. The mixture is stirred for one hour at room temperature, then poured into 200 ml of ice-water, whereupon an oily product separates out, which is left standing to crystallize. The crystals are collected by filtration, washed with water and dried to yield 6.35 g (96.7%) of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-(n-propoxyimino)-acetic acid methyl ester, m.p. 100° C.

Workup

  1. temperaturecooling
  2. waitwhich is left
  3. customto crystallize
  4. filtrationThe crystals are collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7e92283ce4f549afb71abacd8a0a92cd
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

Loading…