Ethane → N-(2-benzylthioethyl)nicotinamide

HRID 1074948

Reaction equation

HRID 1074948 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:12]([S:19][CH2:20][CH2:21][NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC>>[CH2:12]([S:19][CH2:20][CH2:21][NH:22][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 6324EthaneHCID 311982-(Benzylsulfanyl)ethan-1-amineHCID 69188Ethyl Nicotinate

Product 1

HCID 20495567N-(2-benzylthioethyl)nicotinamide

Procedure

30 grams of ethyl nicotinate and 80 grams of 2-benzylthio ethylamine are heated for 12 hours at 170°-180° C. The ethane liberated during the reaction is removed by means of a Dean Stark apparatus. After cooling, the reaction mixture is dissolved in 400 cc of carbon tetrachloride; by addition of petroleum ether, the N-(2-benzylthioethyl)nicotinamide crystallizes: 47 g. By crystallization in a mixture of carbon tetrachloride and cyclohexane, there are recovered colorless crystals of the above product melting at 79° C.

Workup

  1. customis removed by means of a Dean Stark apparatus
  2. temperatureAfter cooling
  3. dissolutionthe reaction mixture is dissolved in 400 cc of carbon tetrachloride
  4. additionby addition of petroleum ether
  5. customthe N-(2-benzylthioethyl)nicotinamide crystallizes
  6. customBy crystallization
  7. additionin a mixture of carbon tetrachloride and cyclohexane, there
  8. customare recovered colorless crystals of the above product melting at 79° C.

Sources & evidence

ORD record
ord-ad9243e8516948e18e4b28ea6ec3827a
Source dataset
uspto-grants-1983_07
Patent number
US04394520

Linked notes

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