Water → HCID 68712205, compound

HRID 1820132Notes

Reaction equation

HRID 1820132 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.O>C(O)C>[CH3:11][C:6]1[CH:5]=[C:4]([NH:12][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:23])[F:24])=[CH:22][CH:21]=2)[CH:3]=[C:2]([CH3:1])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 369113,5-Dimethyl-4-nitroanilineHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 68712205HCID 68712205, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Dimethyl-4-nitro-phenylamine (3.95 g) and 4-trifluoromethyl-benzaldehyde (4.87 mL) were dissolved in ethanol (50 mL) and refluxed for 16 h. The reaction mixture was poured into water (75 mL) and the precipitate collected by filtration. Sodium cyanoborohydride (3.1 g) and acetic acid (7.0 mL) were added to the precipitate dispersed in methanol (130 mL) and stirred for 60 minutes. The reaction mixture was filtered, water (350 mL) was added and the organic solvent was removed in vacuo. The product was allowed to precipitate at 25° C. and collected by filtration and washed with water (300 mL) to furnish 6.7 g (85% yield) of the title compound as a yellow solid. LC-MS (m/z) 325 (MH+); tR=2.00, (UV, ELSD) 92%, 93%. 1H NMR (500 MHz, CDCl3): 2.30 (s, 6H), 4.45 (broad, 3H), 6.25 (s, 2H), 7.45 (d, 2H), 7.60 (d, 2H).

Workup

  1. temperaturerefluxed for 16 h
  2. filtrationthe precipitate collected by filtration
  3. additionSodium cyanoborohydride (3.1 g) and acetic acid (7.0 mL) were added to the precipitate
  4. additiondispersed in methanol (130 mL)
  5. filtrationThe reaction mixture was filtered
  6. additionwater (350 mL) was added
  7. customthe organic solvent was removed in vacuo
  8. customto precipitate at 25° C.
  9. filtrationcollected by filtration
  10. washwashed with water (300 mL)

Sources & evidence

ORD record
ord-30900ba695774559a9b4c8f9519664d4
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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