Triethylamine → HCID 20148563, compound

HRID 569066Notes

Reaction equation

HRID 569066 reaction equation
[S:1]([C:5]1[S:13][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br)#[N:15].C(N(CC)CC)C>C(#N)C.O>[S:1]([C:5]1[S:13][C:8]2[CH2:9][N:10]([CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[C:16]([C:14]#[N:15])[CH:17]=3)[CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 201485892-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 20148563HCID 20148563, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a partial suspension of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (2.20 g, 10.1 mmol) in acetonitrile (50 ml) containing 3-cyanobenzylbromide (2.36 g, 12 mmol) was added triethylamine (1.70 ml, 12.2 mmol). After stirring at room temperature for three hours, the clear solution was diluted with water and the product was extracted into ethyl acetate/methanol, dried over anhydrous sodium sulfate, filtered and evaporated to give a residue which was triturated with methylene chloride/diethyl ether to give purified product (3.2 g, 96% yield). Recrystallization from hot ethanol gave product (2.4 g), m.p. 137°-139° C.

Workup

  1. extractionthe product was extracted into ethyl acetate/methanol
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a residue which
  6. customwas triturated with methylene chloride/diethyl ether
  7. customto give

Sources & evidence

ORD record
ord-e4e25f182b43472ebbc01f29642efdb9
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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