Acetic Acid → HCID 178464652, compound

HRID 1044696Notes

Reaction equation

HRID 1044696 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:6][N:5]([C:7]([NH:21][CH2:22][CH3:23])=[N:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)(=[O:11])=[O:10])[N:4]=[CH:3]1.C(O)(=O)C>CCO.O.[Fe]>[NH2:18][C:14]1[CH:13]=[C:12]([S:9]([N:8]=[C:7]([N:5]2[CH2:6][C:2]([CH3:1])([CH3:24])[CH:3]=[N:4]2)[NH:21][CH2:22][CH3:23])(=[O:11])=[O:10])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 178464654HCID 178464654, compound

Product 1

HCID 178464652HCID 178464652, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 50 mL EtOH and 25 mL water, 1.11 g N-[(4,4-Dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-3-nitro-benzenesulfonamide was dissolved. Subsequently, 1.05 g iron and 1.08 mL acetic acid were added, and the mixture was refluxed for 4 h. After cooling to room temperature, the mixture was filtered over Hyflo and the Hyflo was rinsed with MeOH. The alcohols were evaporated from the filtrate, and 5% aqueous NaHCO3 and DCM were added. The material insoluble in these phases was filtered off, the organic phase was separated and the aqueous phase extracted once more with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness to give 1.02 g (100%) of 3-amino-N-[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-benzenesulfonamide as a brown foam. 1H NMR (400 MHz, CDCl3) δ 1.14 (t, J=7.22 Hz, 3H), 1.19 (s, 6H), 3.42-3.51 (m, 2H), 3.73 (s, 2H), 3.93 (br.s., 2H), 6.71-6.79 (m, 2H), 6.90 (br.s., 1H), 7.20 (t, J=7.83 Hz, 1H), 7.24-7.31 (m, 2H).

Workup

  1. dissolutionwas dissolved
  2. temperaturethe mixture was refluxed for 4 h
  3. filtrationthe mixture was filtered over Hyflo
  4. washthe Hyflo was rinsed with MeOH
  5. customThe alcohols were evaporated from the filtrate, and 5% aqueous NaHCO3 and DCM
  6. additionwere added
  7. filtrationThe material insoluble in these phases was filtered off
  8. customthe organic phase was separated
  9. extractionthe aqueous phase extracted once more with DCM
  10. dry with materialThe combined organic layers were dried over MgSO4
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-92157a7aced846cb837248702a8d1342
Source dataset
uspto-grants-2013_10
Patent number
US08563723B2

Reaction notes

Loading…