Sodium Hydroxide → HCID 20308268, compound

HRID 616409Notes

Reaction equation

HRID 616409 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([Br:18])[CH:12]=1)[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.ClCl.[OH-].[Na+]>C(O)(=O)C>[CH3:2][N:3]([CH2:10][C:11]1[CH:16]=[C:15]([Cl:1])[C:14]([OH:17])=[C:13]([Br:18])[CH:12]=1)[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 20308207HCID 20308207, compound

Product 1

HCID 20308268HCID 20308268, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3.6 gm of N-methyl-N-cyclohexyl-3-bromo-4-hydroxy-benzylamine hydrochloride were dissolved in 50 ml of 90% acetic acid and admixed with a solution of 0.75 gm of chlorine in 15 ml of glacial acetic acid while cooling with ice water. After stirring for a short time, the solution was poured into a mixture of ice and 10 N sodium hydroxide solution and extracted three times with methylene chloride. The organic phase was evaporated to dryness. The residue was purified by means of column chromatography over silicagel with ethyl acetate as the eluant, yielding N-methyl-N-cyclohexyl-3-bromo-5-chloro-4-hydroxy-benzylamine, m.p. 136°-138° C, of the formula ##STR29## after recrystallization from ethanol/ether.

Workup

  1. extractionextracted three times with methylene chloride
  2. customThe organic phase was evaporated to dryness
  3. customThe residue was purified by means of column chromatography over silicagel with ethyl acetate as the eluant

Sources & evidence

ORD record
ord-2b1fa3159d4f4678b9f04cd7568d8557
Source dataset
uspto-grants-1978_02
Patent number
US04073942

Reaction notes

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