Thionyl Chloride → 3,4-Dimethoxy-5-nitrobenzoyl chloride

HRID 725365Notes

Reaction equation

HRID 725365 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6](O)=[O:7].S(Cl)([Cl:19])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:19])=[O:7]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 219286243,4-Dimethoxy-5-nitrobenzoic acid

Product 1

HCID 219286153,4-Dimethoxy-5-nitrobenzoyl chloride

Procedure

9.5 g of 3,4-dimethoxy-5-nitrobenzoic acid are suspended in 95 ml of thionyl chloride. The suspension is stirred at 80° for 1 hour. By two-fold evaporation with the addition of absolute toluene there are obtained 10 g of 3,4-dimethoxy-5-nitrobenzoyl chloride which is dissolved in 100 ml of tetrahydrofuran. This solution is added dropwise to 300 ml of 28 percent aqueous ammonia. The mixture is subsequently stirred at 40° for 2 hours and cooled to 5°. The crystalline precipitate is filtered off. There is obtained 3,4-dimethoxy-5-nitrobenzamide of m.p. 182°-185°.

Workup

  1. customBy two-fold evaporation
  2. additionwith the addition of absolute toluene

Sources & evidence

ORD record
ord-1c9632578d474d74b6264646d6a85ad0
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

Loading…