Sulfuric Acid → 2,6-Dichloro-4-methylbenzamide

HRID 280646Notes

Reaction equation

HRID 280646 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].S(=O)(=O)(O)[OH:13]>>[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]([NH2:5])=[O:13]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 136496782,6-Dichloro-4-methylbenzonitrile

Product 1

HCID 136496812,6-Dichloro-4-methylbenzamideYield 59%

Procedure

To stirred, cooled concentrated sulfuric acid (40 ml) was added in portions 2,6-dichloro-4-methylbenzonitrile (13.2 g, 71.0 mmol). The mixture was heated on a steam bath for 3 hours with occasional shaking, cooled, poured into ice-water, and extracted twice with dichloromethane. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (390 g) eluted with 4:1 (v/v) dichloromethane-diethyl ether to provide 8.6 g (59%) of 2,6-dichloro-4-methylbenzamide, m.p. 101°-107° C.

Workup

  1. temperatureThe mixture was heated on a steam bath for 3 hours with occasional shaking
  2. temperaturecooled
  3. extractionextracted twice with dichloromethane
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on a column of silica gel (390 g)
  8. washeluted with 4:1 (v/v) dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-86059a1560274fa6b6651c7a841f8c25
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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