Triethylamine → HCID 21286881, compound

HRID 1577582Notes

Reaction equation

HRID 1577582 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(N(CC)CC)C.[Br:22][CH2:23][C:24](Br)=[O:25]>C(Cl)Cl>[C:7]([O:6][C:4]([C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=1[NH:1][C:24](=[O:25])[CH2:23][Br:22])=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 3430448tert-Butyl 2-aminobenzoate

Product 1

HCID 21286881HCID 21286881, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 2-aminobenzoate (5.79 g.), triethylamine (3.99 g.) in methylene chloride (100 ml.) was added dropwise bromoacetyl bromide (8.01 g.) over a period of 15 minutes with stirring under ice-cooling at 5° to 10° C. followed by stirring for 1.75 hours at the same temperature. The reaction mixture was washed successively with 1 M aqueous solution of citric acid (50 ml.×2), water a satirated aqueous solution of sodium bicarbonate (25 ml.×2), water and an aqueous solution of sodium chloride, dried over magnesium, treated with activated charcoal and then evaporated to give an oil of the title compound (9.65 g.).

Workup

  1. temperaturecooling at 5° to 10° C.
  2. stirringby stirring for 1.75 hours at the same temperature
  3. washThe reaction mixture was washed successively with 1 M aqueous solution of citric acid (50 ml.×2), water a satirated aqueous solution of sodium bicarbonate (25 ml.×2), water
  4. dry with materialan aqueous solution of sodium chloride, dried over magnesium
  5. additiontreated with activated charcoal
  6. customevaporated

Sources & evidence

ORD record
ord-e93aa690148546d783aef1bd910bc550
Source dataset
uspto-grants-1981_09
Patent number
US04288435

Reaction notes

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