Acetic Acid → 3-Amino-N,N-dimethyl-4-[2-(3-thienyl)-1H-imidazol-1-yl]-benzamide

HRID 576841Notes

Reaction equation

HRID 576841 reaction equation
[CH3:1][N:2]([CH3:24])[C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[C:6]([N+:20]([O-])=O)[CH:5]=1.C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+].N>O1CCCC1.C(OCC)(=O)C.O>[NH2:20][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1)[C:3]([N:2]([CH3:24])[CH3:1])=[O:23]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 24477Sodium ThiosulfateHCID 59198669N,N-dimethyl-3-nitro-4-[2-(3-thienyl)-1H-imidazol-1-yl]benzamide

Product 1

HCID 591988023-Amino-N,N-dimethyl-4-[2-(3-thienyl)-1H-imidazol-1-yl]-benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1.60 g of N,N-dimethyl-3-nitro-4-[2-(3-thienyl)-1H-imidazol-1-yl]benzamide, 5.8 mL of acetic acid and 5.8 mL of water were added, and dissolved under heating. To the solution 3.25 g of 85% sodium hyposulfite was added little by little, followed by 3.3 hours' heating under reflux. The reaction liquid was cooled with ice, to which ethyl acetate was added, and then 25% aqueous ammonia was added little by little to render the same weakly alkaline. Tetrahydrofuran was added and whereby separated organic layer was recovered, which was washed with brine and dried over magnesium sulfate. Distilling the solvent off, 769 mg of the title compound was obtained.

Workup

  1. dissolutiondissolved
  2. temperatureunder heating
  3. temperature' heating
  4. temperatureunder reflux
  5. customThe reaction liquid
  6. additionwas added
  7. customwhereby separated organic layer
  8. customwas recovered
  9. washwhich was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. distillationDistilling the solvent off, 769 mg of the title compound
  12. customwas obtained

Sources & evidence

ORD record
ord-aadee00241ed4de5870f8a1465c14a94
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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