Ammonia → 2-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

HRID 515142Notes

Reaction equation

HRID 515142 reaction equation
[CH2:1]([S:3][C:4]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:9]=[C:8]([CH3:18])[C:5]=1[C:6]#[N:7])[CH3:2].N.S(=O)(=O)(O)[OH:21]>O>[CH2:1]([S:3][C:4]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:9]=[C:8]([CH3:18])[C:5]=1[C:6]([NH2:7])=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 866997232-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzonitrile

Product 1

HCID 866997242-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzonitrile (0.30 g, 1.14 mmol) in concentrated sulfuric acid (15 ml) is stirred at 100° C. for 4 h. After completion of the reaction (monitored by TLC), the reaction mixture is diluted with water (30 ml), basified with aqueous ammonia, and extracted with ethyl acetate (3×15 ml). The organic layer is washed with water (20 ml), brine (15 ml), dried over anhydrous sodium sulfate and evaporated to get 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide, which is used in the next step without further purification (0.26 g, 0.92 mmol, 81%).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe organic layer is washed with water (20 ml), brine (15 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-3d3811e958cb466d9a212f634c6aa6ae
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

Loading…