4-Chloroaniline → HCID 66927432, compound

HRID 1920089Notes

Reaction equation

HRID 1920089 reaction equation
N1([CH:10]([NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[C:11]([CH3:14])([CH3:13])[CH3:12])C2C=CC=CC=2N=N1.ClC1C=CC(N)=CC=1.[C:33]([O-])([O-])=[O:34].[K+].[K+]>CO.C1COCC1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][CH:10]([O:34][CH3:33])[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:24])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 11430Potassium CarbonateHCID 18770516HCID 18770516, compound

Product 1

HCID 66927432HCID 66927432, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-2,2-dimethylpropyl)-4-bromobenzamide 120 as a white solid (2.38 mmol), 4-chloroaniline (0.64 g, 5.0 mmol), and K2CO3 (1 g, 7.23 mmol) in methanol (20 mL) and THF (2 mL) was stirred for 18 h at room temperature. The reaction was quenched with 2M HCl and extracted with ether. The organic solution was concentrated onto silica gel and chromatography (9:1 hexanes:ethyl acetate) and gave 4-bromo-N-(1-methoxy-2,2-dimethylpropyl)benzamide and the title product. The product was titrated with ether to give pure 4-bromo-N-(1-(4-chlorophenylamino)-2,2-dimethylpropyl)benzamide (Compound-38) (104 mg, 11%). 1H NMR (300 MHz, d6-DMSO): δ=8.34 (d, J=8.4 Hz, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H), 6.71 (J=8.7 Hz, 2H), 5.81 (d, J=6.6 Hz, 1H), 5.19 (t, J=3.9 Hz, 1H), 1.03 (s, 9H).

Workup

  1. customThe reaction was quenched with 2M HCl
  2. extractionextracted with ether
  3. concentrationThe organic solution was concentrated onto silica gel and chromatography (9:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-c95b27d9392f4ef6b46682b593a02942
Source dataset
uspto-grants-2012_05
Patent number
US08168795B2

Reaction notes

Loading…