Water → HCID 879767, compound

HRID 2236073Notes

Reaction equation

HRID 2236073 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([O-:12])(O)=O.[Na+].O.[C:15]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1C(Cl)=O)([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:9](=[O:12])[C:25]1[CH:26]=[CH:27][C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:20][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 119922-BromoanilineHCID 516892Sodium BicarbonateHCID 137671862-tert-Butylbenzoyl chloride

Product 1

HCID 879767HCID 879767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
35 °C

Procedure

2-Bromoaniline (98%, Oakwood 005347, 214 g, 1.25 mol), NaHCO3 (270 g, 3.2 mol), THF (500 mL) and water (500 mL) were placed into a 5-L round-bottom flask equipped with an overhead stirrer, thermometer and a 500-mL addition funnel. Solution of t-butyl benzoyl chloride (>98%, Fluka 19660, 250 mL, 1.37 mol) in 250 mL of THF was placed into the addition funnel and was added slowly (in 25 min) to the stirred mixture of reagents in the flask. (No external heating or cooling was administered, slight exotherm was observed raising the temperature inside the flask to 35° C.).

Workup

  1. customequipped with an overhead stirrer
  2. additionthermometer and a 500-mL addition funnel
  3. additionwas added slowly (in 25 min)
  4. additionto the stirred mixture of reagents in the flask
  5. temperature(No external heating
  6. temperaturecooling

Sources & evidence

ORD record
ord-82791fdf6cfb4fb7bf2a1cba1bbbd54e
Source dataset
uspto-grants-2010_05
Patent number
US07714130B2

Reaction notes

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