Chloroacetyl chloride → HCID 19974184, compound

HRID 2210365Notes

Reaction equation

HRID 2210365 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([NH:21][CH2:22][CH:23]([OH:32])[C:24]2[N:25]=[C:26]([CH:29]([CH3:31])[CH3:30])[S:27][CH:28]=2)[CH3:20])=[CH:14][CH:13]=1)=[O:9].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:8]([CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH:19]([N:21]2[C:3](=[O:4])[CH2:2][O:32][CH:23]([C:24]3[N:25]=[C:26]([CH:29]([CH3:31])[CH3:30])[S:27][CH:28]=3)[CH2:22]2)[CH3:20])=[CH:16][CH:17]=1)([O:7][CH3:6])=[O:9]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 19974363HCID 19974363, compound

Product 1

HCID 19974184HCID 19974184, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

0.60 ml (7.89 mmol) of chloroacetyl chloride is added dropwise to a stirred solution of 3.10 g (7.89 mmol) of N-[2-(4-methoxycarbonylmethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-isopropyl-thiazol-4-yl)-ethanamine and 1.10 ml (7.89 mmol) of triethylamine in 20 ml of chloroform at 25° C. internal temperature. After the mixture has stood overnight at 20° C., it is concentrated in vacuo, and the resudue is dissolved in 30 ml of anhydrous dimethyl formamide. To this is added 0.888 g (15.78 mmol) of a 55% dispersion of sodium hydride in oil, during which brief foaming is observed. The mixture is stirred at 20° C. for 3 hours, concentrated in vacuo, and the residue is partitioned between water and ether. The ether solution is dried, filtered and concentrated in vacuo, and the oily residue is purified on silica gel (toluene/acetone =4:1).

Workup

  1. concentrationit is concentrated in vacuo
  2. dissolutionthe resudue is dissolved in 30 ml of anhydrous dimethyl formamide
  3. additionTo this is added 0.888 g (15.78 mmol) of a 55% dispersion of sodium hydride in oil
  4. concentrationconcentrated in vacuo
  5. customthe residue is partitioned between water and ether
  6. dry with materialThe ether solution is dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customthe oily residue is purified on silica gel (toluene/acetone =4:1)

Sources & evidence

ORD record
ord-fed16065e23642739ff959c74a2f3a8f
Source dataset
uspto-grants-1995_10
Patent number
US05457205

Reaction notes

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