Water → HCID 67300552, compound

HRID 572912Notes

Reaction equation

HRID 572912 reaction equation
[CH:1]1([CH2:18]C2C=C(C)C=CC=2S([O-])(=O)=O)[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2C=C(C)C=CC=2S([O-])(=O)=O)[CH2:2]1.O.[C-]#[N:32].[Na+].C[N:35]([CH:37]=O)C>>[CH:1]1([CH2:18][C:37]#[N:35])[CH2:5][CH2:4][CH:3]([CH2:6][C:7]#[N:32])[CH2:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 86719091HCID 86719091, compound

Product 1

HCID 67300552HCID 67300552, compound

Conditions

Temperature
150 °C

Procedure

Cyclopentane-1,3-diylbis(methylene)bis(4-methylbenzenesulfonate) 1-21 (1 equivalent) was taken in DMF:H2O mixture (3:1) and sodium cyanide (6 equivalents) was added and stirred at 150° C. for 15 h. The progress of the reaction was monitored by TLC. After completion of the reaction, reaction mixture was quenched with water, extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified to afford the desired product I-22.

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. customwas quenched with water
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-087cf9e8c626491a88404157b37d2990
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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