Water → 8-(2-chloroethylureido)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

HRID 1653806Notes

Reaction equation

HRID 1653806 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[NH2:7][C:8]1[C:17]2[O:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:14]([CH3:24])[C:13](=[O:25])[C:12]=2[CH:11]=[CH:10][CH:9]=1.O>CN(C)C=O>[Cl:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][C:8]1[C:17]2[O:16][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:14]([CH3:24])[C:13](=[O:25])[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 160352-Chloroethyl isocyanateHCID 199728088-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Product 1

HCID 677147128-(2-chloroethylureido)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 ml of 2-chloroethylisocyanate were added, under stirring at ambient temperature, to a solution of 3.9 g of 8-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran in 52 ml of anhydrous dimethylformamide. Stirring was continued at 70° C. for 5 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic phase was evaporated to dryness in vacuo. The residue was suspended in diethyl ether under stirring. The title product was then filtered off and recrystallized from methanol. Yield 3.74 g, m.p. 213°-214° C.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe organic phase was evaporated to dryness in vacuo
  3. stirringunder stirring
  4. filtrationThe title product was then filtered off
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-81482fa0ddb3468c87683afc045d9e6e
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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