Chloroacetyl chloride → HCID 10447619, compound

HRID 2291913Notes

Reaction equation

HRID 2291913 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH:7]1[NH:11][CH2:10][CH2:9][S:8]1.C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>ClCCCl>[Cl:23][CH2:24][C:25]([N:11]1[CH2:10][CH2:9][S:8][CH:7]1[CH2:6][O:5][C:4]1[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=1[O:2][CH3:1])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 30254542-[(2-Methoxyphenoxy)methyl]-1,3-thiazolidine

Product 1

HCID 10447619HCID 10447619, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 2-(o-methoxyphenoxymethyl)thiazolidine (100 g) in 1,2-dichloroethane (250 ml) cooled at 10° is heated, under stirring, with triethylamine (68 ml) and a solution of α-chloroacetylchloride (36.2 ml) in 1,2-dichloroethane (50 ml) is added dropwise. After 1 hour, the mixture is washed with water, dried on Na2SO4 and evaporated to dryness. Subsequent crystallization from propan-2-ol gives 3-α-chloroacetyl-2-(o-methoxyphenoxymethyl)thiazolidine m.p. 87°-88° C. (100 g).

Workup

  1. temperatureis heated
  2. washthe mixture is washed with water
  3. customdried on Na2SO4
  4. customevaporated to dryness
  5. customSubsequent crystallization from propan-2-ol

Sources & evidence

ORD record
ord-0e386782220345c289cb4ab3d60af855
Source dataset
uspto-grants-1989_01
Patent number
US04798898

Reaction notes

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