Phenylacetyl chloride → Methyl 5-bromo-2-(2-phenylacetamido)benzoate

HRID 526825Notes

Reaction equation

HRID 526825 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CCN(CC)CC.[C:20]1([CH2:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:27](=[O:28])[CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 7679Phenylacetyl chloride2×HCID 8471Triethylamine2×HCID 11430Potassium CarbonateHCID 736224Methyl 2-amino-5-bromobenzoate

Product 1

HCID 19168685Methyl 5-bromo-2-(2-phenylacetamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 2-amino-5-bromobenzoate (9.00 g, 39.1 mmol) and Et3N (7.6 mL, 54.8 mmol) in CH2Cl2 (90 mL) was added 2-phenylacetyl chloride (7.26 g, 46.9 mmol) at 4° C. dropwise. After completion of the addition, the cooling bath was removed and the mixture was stirred for 27 hours. TLC showed some of the starting material methyl 2-amino-5-bromobenzoate still remained. More 2-phenylacetyl chloride (1.88 g, 12.2 mmol) and Et3N (2.2 mL, 15.9 mmol) were added, and the mixture was stirred overnight. K2CO3 (aqueous) was added, the organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, dried (Na2SO4), filtered, and concentrated in vacuo. CH3CN (100 mL) was added, and the precipitated solid was filtered, washed with Et2O, and dried to provide the title compound. The filtrate was concentrated in vacuo, and the solid was filtered, washed with Et2O, and dried to provide additional title compound.

Workup

  1. additionAfter completion of the addition
  2. customthe cooling bath was removed
  3. stirringthe mixture was stirred overnight
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. additionCH3CN (100 mL) was added
  11. filtrationthe precipitated solid was filtered
  12. washwashed with Et2O
  13. customdried

Sources & evidence

ORD record
ord-785fba210f2445b69b3db2bd0c559923
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

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