N,N-Dimethylaniline → 6-Bromo-N-(3,5-dichloro-4-hydroxyphenyl)hexanamide

HRID 1762882Notes

Reaction equation

HRID 1762882 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.CN(C)C1C=CC=CC=1.[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>>[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1)=[O:27]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 800374-Amino-2,6-dichlorophenolHCID 898486-Bromohexanoyl chloride

Product 1

HCID 145005106-Bromo-N-(3,5-dichloro-4-hydroxyphenyl)hexanamideYield 89%

Procedure

was prepared in 89% yield from 24.4 g (0.14 mol) of 4-amino-2,6-dichlorophenol, 18.1 g (0.15 mol) of N,N-dimethylaniline and 28.8 g (0.14 mol) of 6-bromohexanoyl chloride according to the procedure of Example 6, part a, except that the reaction was cooled on ice during the addition and was stirred at room temperature rather than refluxed. The product was crystallized from ethanol-water, mp 113°-114° C.

Workup

  1. temperaturewas cooled on ice during the addition
  2. temperaturethan refluxed
  3. customThe product was crystallized from ethanol-water, mp 113°-114° C.

Sources & evidence

ORD record
ord-9a8ad80af68d4f1ba775d67826b01cab
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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