Water → HCID 86734156, compound

HRID 1729963Notes

Reaction equation

HRID 1729963 reaction equation
[OH-].[K+].[Br:3][C:4](=[C:7]1[NH:11][C:10](=[O:12])[NH:9][C:8]1=[O:13])[CH2:5][CH3:6].[C:14]([CH:20](Cl)[C:21]([NH:23][C:24]1[CH:29]=[C:28]([NH:30][C:31](=[O:52])[CH:32]([O:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]([CH2:45][CH3:46])([CH3:44])[CH3:43])=[CH:38][C:37]=2[C:47]([CH2:50][CH3:51])([CH3:49])[CH3:48])[CH2:33][CH3:34])[CH:27]=[CH:26][C:25]=1[Cl:53])=[O:22])(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].O>CO.CN(C)C=O>[C:14]([CH:20]([N:9]1[C:8](=[O:13])[C:7](=[C:4]([Br:3])[CH2:5][CH3:6])[NH:11][C:10]1=[O:12])[C:21]([NH:23][C:24]1[CH:29]=[C:28]([NH:30][C:31](=[O:52])[CH:32]([O:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]([CH2:45][CH3:46])([CH3:43])[CH3:44])=[CH:38][C:37]=2[C:47]([CH2:50][CH3:51])([CH3:49])[CH3:48])[CH2:33][CH3:34])[CH:27]=[CH:26][C:25]=1[Cl:53])=[O:22])(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 21498489HCID 21498489, compoundHCID 74377252HCID 74377252, compound

Product 1

HCID 86734156HCID 86734156, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution containing 4 g of potassium hydroxide dissolved in 15 ml of methanol, was added a solution containing 17 g of 5-α-bromo-n-propylidenehydantoin dissolved in 50 ml of dimethylformamide, and further was added dropwise a solution containing 25 g of α-pivaloyl-α-chloro-2'-chloro-5'-[α-(2,4-di-tert-amylphenoxy)butyramido]acetanilide dissolved in 250 ml of dimethylformamide. After being stirred for 2 hours at room temperature, the reaction mixture was poured into 2 liters of water, and extracted with 1 liter of ethyl acetate. The ethyl acetate layer was separated, washed with a dilute hydrochloric acid solution, washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure, and the residue was recrystallized from a solvent mixture of n-hexane and ethyl acetate, yielding 18 g of the coupler. The melting point was 129° to 131° C.

Workup

  1. additionwas added a solution
  2. additionfurther was added dropwise a solution
  3. extractionextracted with 1 liter of ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. washwashed with a dilute hydrochloric acid solution
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe ethyl acetate was distilled off under reduced pressure
  9. customthe residue was recrystallized from a solvent mixture of n-hexane and ethyl acetate
  10. customyielding 18 g of the coupler

Sources & evidence

ORD record
ord-ffc1806cb88b4f80a7b9d928e5b79d92
Source dataset
uspto-grants-1976_11
Patent number
US03990896

Reaction notes

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