Dimethylformamide → HCID 118184939, compound

HRID 2177407Notes

Reaction equation

HRID 2177407 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([C:15]([F:18])([F:17])[F:16])[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:19][N:20](C)C=O.C([Cu])#N>C(OCC)(=O)C>[OH:14][CH2:13][C:12]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:19]#[N:20])=[CH:3][CH:4]=2)=[N:9][S:10][C:11]=1[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 118184946HCID 118184946, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 118184939HCID 118184939, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Into a 50-mL round-bottom flask was placed [3-(4-iodophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol (148 mg, 0.38 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL), CuCN (52 mg). The resulting solution was stirred overnight at 130° C. in an oil bath. The resulting solution was diluted with 15 mL of ethyl acetate. The resulting mixture was washed with 5×10 mL of saturated aqueous sodium chloride solution. The mixture was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was applied to a silica gel column with ethyl acetate/petroleum ether (17:83), to afford 68 mg (62%) of 4-[4-(hydroxymethyl)-5-(trifluoromethyl)-1,2-thiazol-3-yl]benzonitrile as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. washThe resulting mixture was washed with 5×10 mL of saturated aqueous sodium chloride solution
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50bb3a7f1dfe463fa8cacc819c94a8c4
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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