Triethylamine → HCID 21440213, compound

HRID 328974Notes

Reaction equation

HRID 328974 reaction equation
[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[S:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:28](CC)CC)[CH3:27]>CC(C)=O>[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([O:14][CH2:27][C:26]#[N:28])=[O:13])=[CH:10][C:9]=1[S:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54516912HCID 54516912, compound

Product 1

HCID 21440213HCID 21440213, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-benzyl-3-n-butylthio-5-sulfamylbenzoic acid (0.78 g) chloroacetonitrile (0.17 g), triethylamine (0.42 g) and dry acetone (10 ml) is refluxed for 6 hours. After cooling, the separated triethylamine hydrochloride is removed by filtration, and the filtrate is evaporated in vacuo. The residue is crystallized by trituration with aqueous ethanol. After cooling the material is collected by filtration, washed with cold aqueous ethanol and dried. After recrystallization from aqueous ethanol, cyanomethyl 4-benzyl-3-n-butylthio-5-sulfamylbenzoate is obtained with a melting point of 112.5°-114° C.

Workup

  1. temperatureis refluxed for 6 hours
  2. temperatureAfter cooling
  3. customthe separated triethylamine hydrochloride is removed by filtration
  4. customthe filtrate is evaporated in vacuo
  5. customThe residue is crystallized by trituration with aqueous ethanol
  6. temperatureAfter cooling the material
  7. filtrationis collected by filtration
  8. washwashed with cold aqueous ethanol
  9. customdried
  10. customAfter recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-190a4c46d8a24ca68955f302c1bba0e8
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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