Sodium Hydroxide → HCID 20378450, compound

HRID 2052019Notes

Reaction equation

HRID 2052019 reaction equation
C([NH:4][CH2:5][CH:6]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH:7]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:8][NH:9]C(=O)C)(=O)C.[OH-].[Na+]>>[NH2:4][CH2:5][CH:6]([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[CH:7]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:8][NH2:9]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 20378456HCID 20378456, compound

Product 1

HCID 20378450HCID 20378450, compound

Procedure

21.14 g (0.054 mol) of N,N'-diacetyl-1,4-diamino-2-(p-chlorophenyl)-3-(p-methoxyphenyl)-butane in 80 ml of 15% strength aqueous sodium hydroxide solution are heated to 200° C. in an autoclave for 12 hours. After cooling, the mixture is extracted with chloroform and the organic phase is washed with water and then evaporated in a rotary evaporator. Yield of crude product: 13.2 g (79.6% of theory) of a crystalline product. For purification, this product is recrystallised from 200 ml of cyclohexane, then filtered off, washed with cyclohexane and dried in vacuo at 60° C. Yield: 11.55 g (69.6% of theory); melting point: 124°-127° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with chloroform
  3. washthe organic phase is washed with water
  4. customevaporated in a rotary evaporator
  5. customFor purification
  6. customthis product is recrystallised from 200 ml of cyclohexane
  7. filtrationfiltered off
  8. washwashed with cyclohexane
  9. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-ca9e054b64c44599ad0fe345b6afeb4e
Source dataset
uspto-grants-1980_01
Patent number
US04182832

Reaction notes

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