Chloroacetyl chloride → HCID 20027606, compound

HRID 2291914Notes

Reaction equation

HRID 2291914 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([CH2:21][CH3:22])CC)C.ClCC(Cl)=[O:26].[C:28]([O-])(=[S:30])[CH3:29].[K+]>CC(C)=O>[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[N:11]([C:28](=[S:30])[CH2:29][C:21](=[O:26])[CH3:22])[CH2:10][CH2:9][S:8]1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 30254542-[(2-Methoxyphenoxy)methyl]-1,3-thiazolidineHCID 23670855Potassium ethanethioate

Product 1

HCID 20027606HCID 20027606, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2-(o-methoxyphenoxymethyl)thiazolidine (15 g) in acetone (75 ml), cooled at 10° C., under stirring is added with triethylamine (10.5 ml) and dropwise with a solution of α-chloroacetylchloride (5.8 ml) in acetone (15 ml). After 2 hours the mixture is added with potassium thioacetate (35.4 g) and stirring is continued for 2 hours, the mixture is poured in ice and water (250 ml) and the precipitate is filtered and crystallized from EtOH to give 2-(o-methoxyphenoxy)methyl-3-acetylthioacetylthiazolidine (19.8 g, 87% yield) m.p. 89°-91° C.

Workup

  1. stirringstirring
  2. additionthe mixture is poured in ice
  3. filtrationwater (250 ml) and the precipitate is filtered
  4. customcrystallized from EtOH

Sources & evidence

ORD record
ord-0632a7352f294cd7a2761b928975eb82
Source dataset
uspto-grants-1989_01
Patent number
US04798898

Reaction notes

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