Water → HCID 67585480, compound

HRID 613793Notes

Reaction equation

HRID 613793 reaction equation
[H-].[Na+].[CH3:3][C@@H:4]([CH2:7][CH2:8][OH:9])[CH2:5][OH:6].Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.O>CN(C=O)C>[CH3:3][C@@H:4]([CH2:7][CH2:8][O:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH2:5][O:6][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride2×HCID 10866273HCID 10866273, compound

Product 1

HCID 67585480HCID 67585480, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.88 g, 120 mmol) was dispersed in 50 ml DMF and then added with (S)-2-methyl-1,4-butanediol (5.21 g, 50.0 mmol) while being iced with ice. The reaction mixture after being cooled with ice for another one hour was stirred at room temperature for 2 hours and then added with 4-chlorobenzonitrile (15.3 g, 120 mmol), followed by reaction for 20 hours. After completion of the reaction, the reaction mixture was added carefully with 5 ml water to inactivate excess sodium hydride, followed by vacuum-distillation of DMF. After addition of 200 ml water, a precipitate thus obtained was filtrated and recrystallized from 100 ml ethanol thereby providing the intended product (12.5 g, 40.8 mmol, 82%).

Workup

  1. temperatureThe reaction mixture after being cooled with ice for another one hour
  2. customfollowed by reaction for 20 hours
  3. customAfter completion of the reaction
  4. distillationfollowed by vacuum-distillation of DMF
  5. additionAfter addition of 200 ml water
  6. customa precipitate thus obtained
  7. filtrationwas filtrated
  8. customrecrystallized from 100 ml ethanol

Sources & evidence

ORD record
ord-fd3e8b7f3aa94da09afb90c1d9484f2b
Source dataset
uspto-grants-1999_12
Patent number
US06008401

Reaction notes

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