Diethylamine → 2-Amino-5-bromo-N,N-diethylbenzamide

HRID 2279712Notes

Reaction equation

HRID 2279712 reaction equation
[Br:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9]C(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=O.C1COCC1.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20]>>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=1[C:7]([N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[O:9]

Participants

4

Reactant 3

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 509995132-Amino-5-bromo-N,N-diethylbenzamideYield 15%

Procedure

A solution of 5-Bromoisatoic anhydride (2.00 g, 8.26 mmol) in THF (53.62 mL, 661.1 mmol) was treated with diethylamine (1.28 mL, 12.40 mmol) and allowed to stir overnight at rt. The mixture was concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [0→4% MeOH in DCM] to afford 326 mg of the title compound (15%). 1H NMR (400 MHz, CD3OD) δ 7.24 (dd, J=2.27, 8.84 Hz, 1H), 7.13 (d, J=2.27 Hz, 1H), 6.71 (d, J=8.59 Hz, 1H), 3.43 (br. s., 4H), 1.18 (br. s., 6H). MS (ESI): m/z 271.41 [M+H]+. UPLC: tR=1.09 min (UPLC-SQD: analytical—2 min).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-9d8ba238a0374ec6a2fc3a37995e0d3d
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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