Pentane → HCID 18671687, compound

HRID 1057645Notes

Reaction equation

HRID 1057645 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][C:16]#[N:17])=[CH:3][CH:2]=1.CCCCC.[H-].[Na+].Cl.Cl[CH2:27][C:28]1[N:29]=[C:30]([CH3:33])[S:31][CH:32]=1>CN(C=O)C>[CH3:33][C:30]1[S:31][CH:32]=[C:28]([CH2:27][N:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[C:4]([O:14][CH2:15][C:16]#[N:17])[C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:29]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 18671668(9H-Carbazol-4-yloxy)acetonitrile

Product 1

HCID 18671687HCID 18671687, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(9H-Carbazol-4-yloxy)acetonitrile (0.143 g, 0.64 mmol)) is added to a slurry of pentane-washed NaH (0.0825 g, 0.0021 mol) in DMF (1 mL) and allowed to stir for 20 min at room temperature. 4-Chloromethyl-2-methylthiazole hydrochloride (0163 g, 0.89 mmol) is added and after stirring for 2 h the mixture is partitioned between ethyl acetate and water. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (75 mL) using ethyl acetate/hexane (20/80 and 40/60) and solids are crystallized from dichloromethane/ether to give 0.162 g (76%) of the title compound; MS (ESI+) for C19H15N3OS m/z 334.2 (M+H)+; IR (drift) 1581, 1459, 1440, 1341, 1333, 1275, 1228, 1215, 1182, 1157, 1151, 1113, 782, 754, 718 cm−1; 1H NMR (CDCl3) δ2.74, 5.09, 5.62, 6.38, 6.78, 7.19, 7.31, 7.44, 8.32. Anal. Calcd for C19H15N3OS: C, 68.45; H, 4.53; N, 12.60. Found: C, 68.27; H, 4.53; N, 12.33.

Workup

  1. stirringafter stirring for 2 h the mixture
  2. customis partitioned between ethyl acetate and water
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (75 mL)
  6. customare crystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-381f3bae44364e1687db1e3265fac108
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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