Triethylamine → HCID 54460661, compound

HRID 581969Notes

Reaction equation

HRID 581969 reaction equation
[CH:1](=[N:23][OH:24])[C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][N:16]=4)[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.ClN1C(=O)C[CH2:28][C:27]1=O.C(Br)=C.C(N(CC)CC)C>CN(C=O)C.O>[O:24]1[CH:28]=[CH:27][C:1]([C:2]2[CH:22]=[CH:21][C:5]3[N:6]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([C:15]5[CH:20]=[CH:19][N:18]=[CH:17][N:16]=5)[CH:10]=4)[CH:7]=[N:8][C:4]=3[CH:3]=2)=[N:23]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11641BromoetheneHCID 31398ChlorosuccinimideHCID 86754224HCID 86754224, compound

Product 1

HCID 54460661HCID 54460661, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 42a (2.1 g) and N-chlorsuccinimide (1.1 g, 1.2 equivalents) in DMF (100 ml) was stirred under argon at 60° C. for 0.5 hours. Vinyl bromide (25 ml) was added to the reaction mixture under ice-cooling, and thereafter triethylamine (4.8 ml, 5 equivalents) in 15 ml DMF was added dropwise over one hour. The mixture was stirred at 0° C. for 3 hours and at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried, and concentrated under reduced pressure. The residue was purified by column-chromatography on silica gel using a mixture of CH2Cl2 and methanol (30:1) as the eluent to give 5-(3-isoxazolyl)-1-(3-(4-pyrimidinyl)phenyl)benzimidazole (1.5 g, 64%).M.p. 214-215° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at 0° C. for 3 hours and at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column-chromatography on silica gel using
  8. additiona mixture of CH2Cl2 and methanol (30:1) as the eluent

Sources & evidence

ORD record
ord-0d285be8f8604e37ae40df36c710607e
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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