Dimethylformamide → HCID 67794197, compound

HRID 982082Notes

Reaction equation

HRID 982082 reaction equation
[C-]#N.[K+].Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:14]1.[CH3:36][N:37](C=[O:40])C>O.C(OCC)(=O)C.CCCCCC.C(N(CC)CC)C>[OH2:40].[C:30]1([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:36]#[N:37])[N:14]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:30]1([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:36]#[N:37])[N:14]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 15725751HCID 15725751, compound

Product 1

HCID 67794197HCID 67794197, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of potassium cyanide (0.4 g, 6.1 mmol), 1-(8-bromooctyl)-3,4,5-triphenyl-lH-pyrazole (2.70 g, 5.5 mmol) and DMF (30 mL was heated at 70° C. under an atmosphere of nitrogen. After 58 hours, the reaction mixture was diluted with water and extracted with dichloromethane (3 x). The combined extracts were washed with water, saturated sodium chloride solution, dried over sodium sulfate and concentrated to leave an oil. Chromatography on a column of silica gel using a mixture ethyl acetate, hexane and triethylamine (20:79:1) as eluent gave 3,4,5-triphenyl-lH-pyrazole-1-nonanenitrile hemihydrate (1.27 g, 52%) as a beige solid. An analytical sample, recrystallized from a mixture of dichloromethane and hexane, had m.p.=79.5°-80.5° C. MS(CI): m/e =434 (MH+).

Workup

  1. extractionextracted with dichloromethane (3 x)
  2. washThe combined extracts were washed with water, saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto leave an oil

Sources & evidence

ORD record
ord-a0ce79b630ca448ea1aa4d0ed9246a83
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

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