Reaction #1128005

Reaction equation

carbamoyl chloride

7-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitric acid salt

triethylamine

→

7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-carboxylic acid dimethylamide

Yield 85.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   OtherPurification by silica gel chromatography

Procedure

7-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitric acid salt (100 mg, 0.394 mmol) was dissolved CH2Cl2 and triethylamine (119 mg, 166 μL, 1.182 mmol, 3.0 eq) followed by carbamoyl chloride (46.4 mg, 39.7 μL, 0.433 mmol, 1.1 eq) were added. The reaction was stirred at room temperature for 4 hours and then concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-5% MeOH/CH2Cl2 as the eluting solvent to obtain 7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-carboxylic acid dimethylamide as a light orange oil (88 mg, 85%). LCMS (m/e) 264 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.01-7.95 (m, 2H), 7.26 (d, 1H, J=9.3 Hz), 3.45-3.39 (m, 4H), 3.11-3.04 (m, 4H), 2.84 (s, 3H), 2.83 (s, 3H).

Source