Dimethylamine → 2-Amino-5-bromo-N,N-dimethylbenzamide

HRID 2279742Notes

Reaction equation

HRID 2279742 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[C:4]([N:6]([CH2:9]C)[CH2:7]C)=[O:5].CNC>>[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[C:4]([N:6]([CH3:7])[CH3:9])=[O:5]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 509995132-Amino-5-bromo-N,N-diethylbenzamide

Product 1

HCID 509995122-Amino-5-bromo-N,N-dimethylbenzamideYield 73%

Procedure

Prepared analogously to Compound 3D replacing diethylamine with dimethylamine to afford 1.47 g of the title compound (73%). 1H NMR (400 MHz, CD3OD) δ 7.24 (dd, J=2.4, 8.7 Hz, 1H), 7.18 (d, J=2.3 Hz, 1H), 6.70 (d, J=8.8 Hz, 1H), 3.04 (br. s., 6H). MS (ESI): m/z 243.33 [M+H]+. UPLC: tR=0.88 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-3ac183fdd0f846a397fcd724575ca74d
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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