Pyridine → HCID 20316055, compound

HRID 973111Notes

Reaction equation

HRID 973111 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[CH2:13][C:11](=[O:12])[N:10]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[C:8]1=[O:9].N1C=CC=CC=1>C1(C)C=CC=CC=1>[O:9]=[C:8]1[N:10]([CH2:14][N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[C:3](=[O:4])[CH3:2])[C:11](=[O:12])[CH2:13][N:7]1[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 203160711-Methyl-3-(2-methoxyphenylaminomethyl)hydantoin

Product 1

HCID 20316055HCID 20316055, compoundYield 73.3%

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 solution of 7 g of the 1-methyl-3-(2-methoxyphenylaminomethyl)hydantoin and 2.8 g of pyridine in 40 ml of toluene at -10° C. The suspension was stirred on an ice-bath for 1.5 hrs. The resulting precipitate was filtered and thoroughly washed with 5% hydrochloric acid, water, and recrystallized from chloroformether to give 6.0 g of N-(2,4-dioxo-1-methylimidazolidin-3-ylmethyl)-N-(2-methoxyphenyl)acetamide, mp 169°-172° C; M+ = 325.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washthoroughly washed with 5% hydrochloric acid, water
  3. customrecrystallized from chloroformether

Sources & evidence

ORD record
ord-bccea100dd4647d0b646cb14ee395b48
Source dataset
uspto-grants-1977_10
Patent number
US04055410

Reaction notes

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