Sodium Iodide → HCID 19375003, compound

HRID 128725Notes

Reaction equation

HRID 128725 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:4]([NH:16]C(=O)C2C(C)=CC=CC=2C)=[N:3]1.[I-].[Na+].B(F)(F)F.CCOCC>C(#N)C>[NH2:16][C:4]1[CH:5]=[C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8000Boron trifluoride etherateHCID 19374999HCID 19374999, compound

Product 1

HCID 19375003HCID 19375003, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a cooled (0° C.) suspension of N-(1-methyl-5-benzyloxymethylpyrazol-3-yl)-2,6-dimethyl benzamide (9 g, 0.025M) and sodium iodide (19 g, 0.125M) in acetonitrile (250 ml) was added boron trifluoride etherate (18,3 g, 0,125M) in acetonitrile (60 ml) under nitrogen atmosphere. After being stirred for 2 hours at room temperature and usual work-up, the crude material was purified by column chromatography on silica gel using CH2Cl2, then CH2Cl2 /CH3OH=97.5/2.5 and 95/5 as eluents to give 1.5 g (23%) of a white solid.

Workup

  1. temperatureTo a cooled
  2. customusual work-up, the crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dafa375db4234d0e9cf48ecb0119249b
Source dataset
uspto-grants-1995_11
Patent number
US05464860

Reaction notes

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