3-Aminobenzamide → HCID 17394186, compound

HRID 1625200Notes

Reaction equation

HRID 1625200 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C(N(CC)CC)C.[Br:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C1COCC1>[Br:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5](=[O:6])[NH2:7])[CH:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 16453-AminobenzamideHCID 8471TriethylamineHCID 235422-Bromobenzoyl chloride

Product 1

HCID 17394186HCID 17394186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 3-aminobenzamide (310 mg, 2.3 mmol) in 7.6 mL of THF at 0° C. was added triethyl amine (0.63 mL, 4.6 mmol) followed by 2-bromobenzoylchloride (500 mg, 2.3 mmol). The reaction was stirred at 0° C. for 15 minutes and partitioned between water and dichloromethane. The layers were separated, the organics dried and solvent removed to give 2-bromo-N-(3-carbamoylphenyl)benzamide which was used for coupling without further purification.

Workup

  1. custompartitioned between water and dichloromethane
  2. customThe layers were separated
  3. customthe organics dried
  4. customsolvent removed

Sources & evidence

ORD record
ord-b2c6dde620a54d1e90335665cd7fda0a
Source dataset
uspto-grants-2014_07
Patent number
US08779197B2

Reaction notes

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