Butanamide, N-(3-amino-4-chlorophenyl)-4-[2,4-bis(1,1-dimethylpropyl)phenoxy]- → HCID 20313377, compound

HRID 2419509Notes

Reaction equation

HRID 2419509 reaction equation
[C:1]1([S:7][C:8]([CH3:18])([CH3:17])[C:9]([CH2:11][C:12]([O:14]CC)=O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:19][C:20]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:49])[CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH2:42][CH3:43])([CH3:41])[CH3:40])=[CH:35][C:34]=2[C:44]([CH2:47][CH3:48])([CH3:46])[CH3:45])=[CH:23][C:21]=1[NH2:22]>C1(C)C(C)=CC=CC=1>[Cl:19][C:20]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:49])[CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH2:42][CH3:43])([CH3:41])[CH3:40])=[CH:35][C:34]=2[C:44]([CH2:47][CH3:48])([CH3:46])[CH3:45])=[CH:23][C:21]=1[NH:22][C:12](=[O:14])[CH2:11][C:9](=[O:10])[C:8]([S:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 171044Butanamide, N-(3-amino-4-chlorophenyl)-4-[2,4-bis(1,1-dimethylpropyl)phenoxy]-HCID 54462273HCID 54462273, compound

Product 1

HCID 20313377HCID 20313377, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5.2 g of ethyl (2-Phenylthio-2-methylpropionyl)acetate and 8.8 g of 2-chloro-5-[4-(2,4-di-tert-amylphenoxy)butyramido]aniline in 30 ml of xylene was refluxed for five hours. From the reaction mixture xylene was distilled off, and the residue was recrystallized from acetonitrile to obtain 11.5 g (yield 85%) of Coupler (16) having a melting point of 144° to 145° C.

Workup

  1. temperaturewas refluxed for five hours
  2. distillationFrom the reaction mixture xylene was distilled off
  3. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5667466dbae142a2852e820b2d1ddd12
Source dataset
uspto-grants-1978_08
Patent number
US04106942

Reaction notes

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