Dimethylformamide → HCID 178511243, compound

HRID 1491512Notes

Reaction equation

HRID 1491512 reaction equation
ClS([N:5]=[C:6]=O)(=O)=O.[C@H:8]1(C(O)=O)[CH2:13][CH2:12][C@H:11]([C:14](O)=O)[CH2:10][CH2:9]1.C[N:21](C=O)C>ClCCl>[C@H:8]1([C:6]#[N:5])[CH2:13][CH2:12][C@H:11]([C:14]#[N:21])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 178525731HCID 178525731, compound

Product 1

HCID 178511243HCID 178511243, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

50.4 g (357 mmol) of chlorosulfonyl isocyanate in 30 ml of dichloromethane are added dropwise to 30 g (174 mmol) of trans-cyclohexane-l,4-dicarboxylic acid in 90 ml of dichloromethane under reflux. When the evolution of gas is completed, the mixture is stirred for a further 1.5 hours under reflux. 40 ml (715 mmol) of DMF are subsequently added dropwise at from -15 to -20° C., and the mixture is stirred for a further 15 minutes and hydrolyzed using 300 ml of ice water. The phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed four times with water, dried over MgSO4 and evaporated in vacuo. Crystallization from DMF gives 8.74 g (37.4%) of trans-cyclohexane-l,4-dinitrile.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux
  3. stirringthe mixture is stirred for a further 15 minutes
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with dichloromethane
  6. washThe combined organic phases are washed four times with water
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customCrystallization from DMF

Sources & evidence

ORD record
ord-fb212fd8ead646e092768beb46732e88
Source dataset
uspto-grants-1994_12
Patent number
US05370823

Reaction notes

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