Triethylamine → 4-(1-Bromo-cyclohexanoyl)-amino-2,3-dichloro-phenol

HRID 582721Notes

Reaction equation

HRID 582721 reaction equation
[Br:1][C:2]1([C:8](Cl)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([Cl:19])[C:13]=1[Cl:20].C([N:23](CC)CC)C>O1CCCC1>[Br:1][C:2]1([C:8]([C:12]2[C:17]([NH2:23])=[CH:16][C:15]([OH:18])=[C:14]([Cl:19])[C:13]=2[Cl:20])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98775294-Amino-2,3-dichlorophenolHCID 152548741-Bromocyclohexanecarbonyl chloride

Product 1

HCID 867542704-(1-Bromo-cyclohexanoyl)-amino-2,3-dichloro-phenolYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

12.6 g (0.056 mol) of 1-bromo-cyclohexanecarboxylic acid chloride are added dropwise at 0° C. with stirring to a mixture of 10 g (0.056 mol) of 4-amino-2,3-dichlorophenol and 100 ml of tetrahydrofuran. After adding half (5 g) of the acid chloride, 7.7 ml (0.05 mol) of triethylamine are added dropwise at the same time. When the addition has ended, the reaction mixture is stirred for 24 hours at 20° C. and then poured into 300 ml of ice-water. The mixture is extracted twice using in each case 300 ml of dichloromethane, and the organic phase is dried over magnesium sulphate and evaporated by stripping off the solvent under reduced pressure. The residue which remains is recrystallized from toluene. In this manner. 11.9 g (58% of theory) of 4-(1-bromo-cyclohexanoyl)-amino-2,3-dichloro-phenol are obtained in the form of a solid substance of melting point 142° C.

Workup

  1. additionare added dropwise at the same time
  2. additionWhen the addition
  3. extractionThe mixture is extracted twice
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. customevaporated
  6. customThe residue which remains is recrystallized from toluene

Sources & evidence

ORD record
ord-57ffef8609494f65947386a56af30e3f
Source dataset
uspto-grants-1999_07
Patent number
US05925674

Reaction notes

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