Water → HCID 68711366, compound

HRID 1820130Notes

Reaction equation

HRID 1820130 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([NH2:15])=[CH:8][C:7]=1[CH3:16])[CH3:2].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.O>C(O)C>[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([NH:15][CH2:24][C:23]2[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:28])[F:29])=[CH:27][CH:26]=2)=[CH:8][C:7]=1[CH3:16])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 679964-(Trifluoromethyl)benzaldehydeHCID 86229161HCID 86229161, compound

Product 1

HCID 68711366HCID 68711366, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Amino-2-methyl-6-nitro-phenyl)-carbamic acid ethyl ester (0.50 g) and 4-trifluoromethyl-benzaldehyde (0.29 mL) were dissolved in ethanol (10 mL) and refluxed for 16 h. The reaction mixture was poured into water (75 mL) and the precipitate collected by filtration. Sodium cyanoborohydride (0.3 g) and acetic acid (0.5 mL) were added to the precipitate dispersed in methanol (10 mL) and stirred for 60 minutes. The reaction mixture was filtered, water (50 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 (100 mL) to furnish 0.47 g (75% yield) of the title compound as a yellow solid. LC-MS (m/z) 398 (MH+); tR=3.18, (UV, ELSD) 86%, 94%. 1H NMR (500 MHz, DMSO-d6): 1.20 (1,3H), 2.10 (s, 3H), 4.05 (m, 2H), 4.45 (m, 2H), 6.75 (m, 1H), 6.90 (m, 1H), 7.55 (m, 2H), 7.73 (m, 2H), 8.75 (s, 1H).

Workup

  1. temperaturerefluxed for 16 h
  2. filtrationthe precipitate collected by filtration
  3. additionSodium cyanoborohydride (0.3 g) and acetic acid (0.5 mL) were added to the precipitate
  4. additiondispersed in methanol (10 mL)
  5. filtrationThe reaction mixture was filtered
  6. additionwater (50 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 (100 mL)

Sources & evidence

ORD record
ord-e767245c513648d783b51460a9844c82
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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