Pyridine → HCID 20316054, compound

HRID 2418943Notes

Reaction equation

HRID 2418943 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][CH2:14][N:15]1[C:19](=[O:20])[CH2:18][S:17][C:16]1=[O:21].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:13]([CH2:14][N:15]1[C:19](=[O:20])[CH2:18][S:17][C:16]1=[O:21])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 28441932,4-Thiazolidinedione, 3-[[(2-methylphenyl)amino]methyl]-

Product 1

HCID 20316054HCID 20316054, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4.5 g of chloroacetyl chloride in 10 ml of toluene was added dropwise to a suspension of 7.8 g of N-(2-methylphenylaminomethyl)-2,4-thiazolidinedione and 3 g of pyridine in 80 ml of toluene at -5° C with stirring and kept on an ice bath for 3 hrs. The resulting precipitate was filtered and washed with water to give 2-chloro-N-(2,4-dioxothiazolidin-3-ylmethyl)-N-(2-methylphenyl)acetamide, mp 133°-136° C. The toluene filtrate was extracted with two 50 ml portions of 5% hydrochloric acid, 50 ml of water, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated on a rotary evaporator to give the product which was crystallized from benzene-ether, mp 134°-137° C. The total yield was 6.0 g [M+ = 312 (molecular ion by mass spec.)].

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-6e4e34a796464a92a330b3b8330cbe89
Source dataset
uspto-grants-1978_08
Patent number
US04104051

Reaction notes

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