Thionyl Chloride → N-(2,2-dimethoxyethyl)-2-(dimethylamino)-5-nitrobenzamide

HRID 450099Notes

Reaction equation

HRID 450099 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH2:24].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O.O.CC(C)=O.O>[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH:24][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:3]=1[N:2]([CH3:1])[CH3:15]

Participants

9

Reactant 4

HCID 24386Thionyl ChlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium BicarbonateHCID 28046762-(dimethylamino)-5-nitrobenzoic acid

Product 1

HCID 68829856N-(2,2-dimethoxyethyl)-2-(dimethylamino)-5-nitrobenzamide

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A mixture of 2-dimethylamino-5-nitro benzoic acid (300 mg, 1.42 mmol) and thionyl chloride (0.41 ml 5.7 mmol) in dry chloroform (5 ml) was heated to reflux for 3 hr. The excess thionyl chloride was evaporated to give a residue, which was then dissolved in acetone (2 ml). This was then added drop-wise to a mixture of 2,2-dimethoxy-ethylamine (0.15 ml, 1.44 mmol) and sodium bicarbonate (120 mg, 1.44 mmol) in 2:1 acetone-water (12 ml) at 0° C. and stirred overnight at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and then brine, dried and concentrated to yield of N-(2,2-dimethoxyethyl)-2-dimethylamino-5-nitro benzamide (313 mg, 79%) as solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hr
  3. customThe excess thionyl chloride was evaporated
  4. customto give a residue, which
  5. additionThis was then added drop-wise
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialbrine, dried
  9. concentrationconcentrated to yield of N-(2,2-dimethoxyethyl)-2-dimethylamino-5-nitro benzamide (313 mg, 79%) as solid

Sources & evidence

ORD record
ord-246c45ccd5774bbeab8a5a745b8c7336
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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