Triethylamine → HCID 21286881, compound

HRID 745706Notes

Reaction equation

HRID 745706 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 1M 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 1M 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-00fbfc1485474937b82b548f4123a33d
Source dataset
uspto-grants-1986_07
Patent number
US04599426

Reaction notes

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