Benzyl Isothiocyanate → HCID 17974868, compound

HRID 227227Notes

Reaction equation

HRID 227227 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([NH2:13])=[O:12].[CH2:16]([N:23]=[C:24]=[S:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[CH2:27][CH2:28]Br>CN(C)C=O.O.C(OCC)(=O)C>[CH2:16]([N:23]1[CH2:28][CH2:27][S:25][C:24]1=[N:13][C:11]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[C:4]([F:3])([F:14])[F:15])=[O:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 2346Benzyl IsothiocyanateHCID 78391,2-DibromoethaneHCID 24758Sodium hydride2×HCID 27826434-Trifluoromethylnicotinamide

Product 1

HCID 17974868HCID 17974868, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.09 g, 60% dispersion in mineral oil) was added portionwise to a solution of 4-trifluoromethyl-3-pyridinecarboxamide (0.40 g) in N,N-dimethylformamide at 20° C., and stirred for 1 hour. Benzyl isothiocyanate (0.31 ml) was added and stirred at 20° C. for 1 hour, then 1,2-dibromoethane (0.30 ml) added and stirred at 20° C. for 1 hour. Sodium hydride (0.09 g, 60% dispersion in mineral oil) was added in portions to the solution then stirred for 5 hours. Ethyl acetate and water were added, the organic phase dried (magnesium sulfate), evaporated and the residue purified by silica gel column chromatography eluting with n-hexane/ethyl acetate (3:1) to give 3-benzyl-2-(4-trifluoromethyl-3-pyridylcarbonyl)iminothiazolidine (0.50 g, Compound D-40).

Workup

  1. stirringstirred at 20° C. for 1 hour
  2. stirringstirred at 20° C. for 1 hour
  3. stirringthen stirred for 5 hours
  4. dry with materialthe organic phase dried (magnesium sulfate)
  5. customevaporated
  6. customthe residue purified by silica gel column chromatography
  7. washeluting with n-hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-036db8a18ee341ed87f1a28b6714d5e1
Source dataset
uspto-grants-2009_07
Patent number
US07560456B2

Reaction notes

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