Hydrochloric Acid → HCID 20375553, compound

HRID 1448791Notes

Reaction equation

HRID 1448791 reaction equation
Cl[CH2:2][C:3]1[C:7]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:6][S:5][CH:4]=1.[C-:13]#[N:14].[K+].Cl>C(O)COCCOCCO>[C:13]([CH2:2][C:3]1[C:7]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:6][S:5][CH:4]=1)#[N:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 166399203-chloromethyl-N-methyl-4-thiophenesulfonamide

Product 1

HCID 20375553HCID 20375553, compound

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Procedure

26.5 g (0.109 mol) of 3-chloromethyl-N-methyl-4-thiophenesulfonamide and 21.3 g (0.328 mol) of potassium cyanide are warmed to 80° C. for 20 minutes in 130 ml of triethyleneglycol. Thereafter, the mixture is poured into 200 ml of 2-N hydrochloric acid and 200 g of ice and extracted with three 250 ml portions of methylene chloride. The combined organic phases are dried over sodium sulfate, stirred with 3 g of active carbon, filtered and evaporated. There is obtained 3-cyanomethyl-N-methyl-4-thiophenesulfonamide in the form of a non-crystallizing oil which is used in the next step without further purification.

Workup

  1. extractionextracted with three 250 ml portions of methylene chloride
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-778636f5b4b04dc8b8f7f9579b049101
Source dataset
uspto-grants-1980_02
Patent number
US04187303

Reaction notes

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