Water → HCID 59770937, compound

HRID 2218956Notes

Reaction equation

HRID 2218956 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:6]=2[N:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH3:1][N:2]([CH3:14])[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69218842565237-26-5

Product 1

HCID 59770937HCID 59770937, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2-(Dimethylamino)-1,3-benzoxazole-5-carbonitrile (1.5 g, 8.0 mmol) in 150 mL of dry ether, 640 mg (16.0 mmol) of LiAlH4 were slowly added. The mixture was stirred at room temperature for 1.5 h and the excess of reagent was decomposed by careful addition of the minimum amount of water and filtered. The solids were washed with hot EtOAc (3×100 mL) giving a residue after evaporation. The purification by column chromatography yield 622 mg (41%) of the title compound as a white solid. Rf (CH2Cl2/MeOH 9:1+0.25% NH3) 0.2; 1H NMR (CD3OD) δ 7.23 (s, 1H, H-4), 7.15 (d, 1H, J=8.1 Hz, H-7), 6.89 (d, 1H, J=8.1 Hz, H-6), 3.83 (s, 2H, CH2), 3.14 (s, 6H, CH3×2); 13C NMR (CD3OD) δ 163.7 (C-2), 148.4 (C-7a), 144.2 (C-3a), 139.8 (C-5), 119.6 (C-6), 114.9 (C-4), 108.7 (C-7), 47.1 (CH2), 38.0 (CH3); mass spectrum (ES+): m/e 192.0 (M++1).

Workup

  1. additionwere slowly added
  2. filtrationfiltered
  3. washThe solids were washed with hot EtOAc (3×100 mL)
  4. customgiving a residue
  5. customafter evaporation
  6. customThe purification by column chromatography yield 622 mg (41%) of the title compound as a white solid

Sources & evidence

ORD record
ord-9c781d6039e44671bd04f5b2d46fa87b
Source dataset
uspto-grants-2008_08
Patent number
US07414036B2

Reaction notes

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