Water → HCID 10269103, compound

HRID 1007177Notes

Reaction equation

HRID 1007177 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[N+:11]([C:14]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:15]=1[NH2:16])([O-:13])=[O:12].C(N(CC)CC)C.O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:14]=2[N+:11]([O-:13])=[O:12])=[O:7])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-HCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 10269103HCID 10269103, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-chloronicotinoyl chloride (100 mg, 0.6 mmol) and 2-nitro-4-trifluoromethylaniline (117 mg, 0.6 mmol) in THF (10 ml) was added triethylamine (0.16 ml, 1.1 mmol). The mixture was stirred at room temperature overnight and then diluted with ethyl acetate. Water was added to dissolve the precipitate and the organic phase was separated and washed with water, then dried over anhydrous sodium sulfate. The product was purified by column chromatography to give the title compound as a pale yellow solid. 1H NMR (DMSO-d6): 11.27 (s, 1H), 8.97 (d, J=2.7, 1H), 8.38-8.35 (m, 2H), 8.19 (d, J=8.4, 1H), 7.96 (d, J=8.7, 1H), 7.78 (d, J=8.1, 1H).

Workup

  1. dissolutionto dissolve the precipitate
  2. customthe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-4512b60e73bb437db115316cdf0a88b5
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Reaction notes

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