Ethanol → HCID 14990741, compound

HRID 2166054Notes

Reaction equation

HRID 2166054 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[CH:10][C:9]=2[N+:20]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)C>O>[CH:1]1([NH:7][C:8]2[C:9]([NH2:20])=[CH:10][C:11]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 14990702HCID 14990702, compound

Product 1

HCID 14990741HCID 14990741, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.9 parts of N-cyclohexyl-4-(1H-imidazol-1-ylmethyl)-2-nitrobenzenamine, 22.9 parts of sodium dithionite, 288 parts of ethanol and 240 parts of water was stirred at room temperature. Upon complete reaction, the ethanol layer was evaporated. The aqueous layer was diluted with a potassium carbonate solution. The whole was extracted twice: first with dichloromethane and then with a mixture of trichloromethane and methanol (90:10 by volume). The combined extracts were dried, filtered and evaporated. The residue was taken up in methylbenzene and the solvent was evaporated again, yielding 7 parts (98.0%) of N1 -cyclohexyl-4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine as a residue (int. 186).

Workup

  1. customUpon complete reaction
  2. customthe ethanol layer was evaporated
  3. additionThe aqueous layer was diluted with a potassium carbonate solution
  4. extractionThe whole was extracted twice
  5. additionfirst with dichloromethane and then with a mixture of trichloromethane and methanol (90:10 by volume)
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. customevaporated
  9. customthe solvent was evaporated again

Sources & evidence

ORD record
ord-f74faf7df25b41a09e3be1d65489e2af
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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