Triethylamine → HCID 86757927, compound

HRID 840593Notes

Reaction equation

HRID 840593 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][NH2:8])([O-:3])=[O:2].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[C:20]1[C:24]([C:25](Cl)=[O:26])=[C:23](C)[O:22][N:21]=1.[CH2:29](N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:29][C:10]1[CH:9]=[C:6]([CH2:7][NH2:8])[CH2:5][C:4]([C:25]([C:24]2[C:20]([C:14]3[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:13]=3[Cl:12])=[N:21][O:22][CH:23]=2)=[O:26])([N+:1]([O-:3])=[O:2])[CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1227223-NitrobenzylamineHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

Product 1

HCID 86757927HCID 86757927, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitrobenzylamine (511 mg, 2.71 mmol) and 3-(2-chloro-6-fluorophenyl)-5-methylisoxaz-4-oyl chloride (742 mg, 2.71 mmol) were suspended in 10 mL of dichloromethane and triethylamine was added (0.95 mL, 6.78 mmol). The reaction went clear and was stirred at room temperature for 2 hours. The reaction was then diluted with 100 mL of ethyl acetate and the organic layer was washed twice each with 1N aqueous hydrochloric acid and 1N aqueous sodium hydroxide. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.12 g of the title compound. (>100). MS(IE) m/z 390 (M+1). IR 3280, 1648, 1532, 1349, 1251 cm−1.

Workup

  1. washthe organic layer was washed twice each with 1N aqueous hydrochloric acid and 1N aqueous sodium hydroxide
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f37f6593952b4e88b596f7e4a49e5847
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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