Dimethylformamide → HCID 58524127, compound

HRID 536428Notes

Reaction equation

HRID 536428 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8](C(OC)=O)[CH:9]=[C:10]([CH:11]=[N:12][OH:13])[C:5]=2[N:4]=[N:3]1.ClN1C(=O)CC[C:20]1=[O:25].[Cl:26][C:27]1[CH:32]=[C:31]([C:33]([C:35]([F:38])([F:37])[F:36])=[CH2:34])[CH:30]=[C:29]([Cl:39])[CH:28]=1.C(N(CC)CC)C.CN(C)[CH:49]=[O:50]>O>[CH3:1][N:2]1[C:6]2[C:7]([C:49]([O:25][CH3:20])=[O:50])=[CH:8][CH:9]=[C:10]([C:11]3[CH2:34][C:33]([C:31]4[CH:32]=[C:27]([Cl:26])[CH:28]=[C:29]([Cl:39])[CH:30]=4)([C:35]([F:36])([F:37])[F:38])[O:13][N:12]=3)[C:5]=2[N:4]=[N:3]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 136351080HCID 136351080, compound

Product 1

HCID 58524127HCID 58524127, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-methyl-6-methoxycarbonylbenzotriazole-4-carbaldehyde oxime (0.1 g) in dimethyl formamide (10 ml) was treated with N-chlorosuccinimide (0.17 g) and stirred at 40° C. for 2 h under nitrogen atmosphere. Then reaction mixture was cooled to room temperature and treated with 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (0.47 g) (prepared according to WO 2005/085216) and triethylamine (0.02 ml), stirred at room temperature for 16 h under nitrogen atmosphere, and treated with water (50 ml). The mixture was extracted with ethyl acetate (3×10 ml) and the combined organic layers were dried over sodium sulfate. Evaporation of solvents and purification by column chromatograph gave 3-methyl-4-methoxycarbonyl-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzotriazole (85 mg). 1H-NMR (400 MHz, CDCl3): 8.15 (d, 1H), 8.05 (d, 1H), 7.58 (d, 2H), 7.42 (t, 1H), 4.74 (bd, 1H), 4.60 (s, 1H), 4.38 (bd, 1H), 4.02 (s, 3H). LC-MS: m/z=472.96 (M+H).

Workup

  1. customThen reaction mixture
  2. temperaturewas cooled to room temperature
  3. stirringstirred at room temperature for 16 h under nitrogen atmosphere
  4. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customEvaporation of solvents and purification by column chromatograph

Sources & evidence

ORD record
ord-57c989acd27d442397e0760e1ed79e3e
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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