Acetic Acid → HCID 59198906, compound

HRID 576848Notes

Reaction equation

HRID 576848 reaction equation
[CH:1]1([C:7]2[N:8]([C:12]3[C:21]([N+:22]([O-])=O)=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([O:25][CH3:26])[CH:13]=3)[CH:9]=[CH:10][N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+].N>O1CCCC1.C(OCC)(=O)C.O>[NH2:22][C:21]1[C:12]([N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:13][C:14]([O:25][CH3:26])=[C:15]([CH:20]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 24477Sodium ThiosulfateHCID 59198783Methyl 4-(2-cyclohexyl-1H-imidazol-1-yl)-2-methoxy-5-nitrobenzoate

Product 1

HCID 59198906HCID 59198906, compoundYield 73.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 13.51 g of methyl 4-(2-cyclohexyl-1H-imidazol-1-yl)-2-methoxy-5-nitrobenzoate as synthesized in above Production Example 27, acetic acid 55 mL and water 55 mL were added and heated to form a solution, to which 22.59 g of 87% sodium hyposulfite was added little by little, followed by heating under reflux for 3.2 hours. The reaction liquid was cooled with ice, to which ethyl acetate and tetrahydrofuran were added, and it was rendered weakly alkaline by addition of 25% aqueous ammonia little by little. The organic layer was separated, washed with saturated brine, dried over magnesium sulfate and removed of the solvent by distillation to provide 9.13 g of the title compound.

Workup

  1. additionwere added
  2. temperatureheated
  3. customto form a solution
  4. temperatureby heating
  5. temperatureunder reflux for 3.2 hours
  6. customThe reaction liquid
  7. additionwere added
  8. customThe organic layer was separated
  9. washwashed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. customremoved of the solvent by distillation

Sources & evidence

ORD record
ord-49d7f6cbb5734042bc2dbbb39d3eddb2
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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