Hydrochloric Acid → HCID 18413859, compound

HRID 991420Notes

Reaction equation

HRID 991420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[Br:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH2:17].Cl>O>[Br:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH:17][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 77070Veratroyl chlorideHCID 826072-Bromo-5-nitroaniline

Product 1

HCID 18413859HCID 18413859, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

3,4-Dimethoxybenzoyl chloride (2 g) was added to a stirred solution of 2-bromo-5-nitroaniline (2.17 g) at 25° C. The reaction mixture was heated at 100° C. for 5 hours. After cooling, water (25 ml) and 3M hydrochloric acid (100 ml) were added. The resulting solid was filtered off and washed with water (50 ml) and dried. The solid was triturated under diethyl ether to give N-(2-bromo-5-nitrophenyl)-3,4-dimethoxybenzamide (2.01 g ) as a sandy-coloured solid, m.p. 183-184° C.; NMR Spectrum: (DMSOd6) 3.92(s, 6H), 7.08 (d, 1H), 7.56 (d, 1H), 7.65 (m, 1H), 8.0 (s, 2H), 8.4 (s, 1H), 10.09 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting solid was filtered off
  3. washwashed with water (50 ml)
  4. customdried
  5. customThe solid was triturated under diethyl ether

Sources & evidence

ORD record
ord-5114858ad61442e097bae50643dded98
Source dataset
uspto-grants-2002_10
Patent number
US06465455B1

Reaction notes

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