Water → HCID 22916362, compound

HRID 1376382Notes

Reaction equation

HRID 1376382 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[O:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.[C-:26]#[N:27].[Na+].O>CS(C)=O>[C:26]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[O:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1)#[N:27]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 9978168HCID 9978168, compound

Product 1

HCID 22916362HCID 22916362, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

2-(7-Bromoheptyl)-4,5-diphenyloxazole (13.8 g) in dimethylsulphoxide (80 ml) was added over 45 minutes to a mixture of sodium cyanide (1.87 g) in dimethylsulphoxide (80 ml). The reaction was stirred at 50° C. for 2 h, cooled and poured into water (500 ml ). The aqueous was extracted with diethyl ether (4×250 ml). The ether extracts were combined, washed with water (250 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Column chromatography on silica gel eluted with a hexane: dichloromethane gradient gave 2-(7-cyanoheptyl)-4,5-diphenyloxazole (4.89 g, 41%) as an oil. Found: C, 80.20; H, 7.02; N, 8.13%; C23H24N2O requires: C, 80.31; H, 7.18; n, 8.16%;

Workup

  1. temperaturecooled
  2. extractionThe aqueous was extracted with diethyl ether (4×250 ml)
  3. washwashed with water (250 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness in vacuo
  6. washColumn chromatography on silica gel eluted with a hexane

Sources & evidence

ORD record
ord-327c7bf759524f75b69ab5318cd780b2
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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