Butanamide, N-(3-amino-4-chlorophenyl)-4-[2,4-bis(1,1-dimethylpropyl)phenoxy]- → HCID 20313371, compound

HRID 2419502Notes

Reaction equation

HRID 2419502 reaction equation
[CH2:1]([S:3][C:4]([CH3:14])([CH3:13])[C:5]([CH2:7][C:8]([O:10]CC)=O)=[O:6])[CH3:2].[Cl:15][C:16]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:45])[CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH2:38][CH3:39])([CH3:37])[CH3:36])=[CH:31][C:30]=2[C:40]([CH2:43][CH3:44])([CH3:42])[CH3:41])=[CH:19][C:17]=1[NH2:18]>C1(C)C(C)=CC=CC=1>[Cl:15][C:16]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:45])[CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH2:38][CH3:39])([CH3:37])[CH3:36])=[CH:31][C:30]=2[C:40]([CH2:43][CH3:44])([CH3:42])[CH3:41])=[CH:19][C:17]=1[NH:18][C:8](=[O:10])[CH2:7][C:5](=[O:6])[C:4]([S:3][CH2:1][CH3:2])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 171044Butanamide, N-(3-amino-4-chlorophenyl)-4-[2,4-bis(1,1-dimethylpropyl)phenoxy]-HCID 53934448HCID 53934448, compound

Product 1

HCID 20313371HCID 20313371, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 21.8 g of ethyl (2-ethylthio-2-methylpropionyl)-acetate obtained in Step 1 of Synthesis Example 1, 44.5 g of 2-chloro-5-[4-(2,4-di-tert-amylphenoxy)butyramido]aniline and 500 ml of xylene was refluxed for ten hours. Xylene was distilled off from the reaction mixture, and the residue was recrystallized from acetonitrile to obtain 53 g (yield 87%) of Coupler (2) having a melting point of 121° to 122° C.

Workup

  1. temperaturewas refluxed for ten hours
  2. distillationXylene was distilled off from the reaction mixture
  3. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-6098f444901044b4af022fa5c0b2ae15
Source dataset
uspto-grants-1978_08
Patent number
US04106942

Reaction notes

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