Ammonia → 2-(Ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide

HRID 515155Notes

Reaction equation

HRID 515155 reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:11]=[C:10]([CH3:20])[C:7]=1[C:8]#[N:9])(=[O:5])=[O:4])[CH3:2].N.S(=O)(=O)(O)[OH:23]>O>[CH2:1]([S:3]([C:6]1[CH:13]=[C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH:11]=[C:10]([CH3:20])[C:7]=1[C:8]([NH2:9])=[O:23])(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 866997302-(Ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzonitrile

Product 1

HCID 866997322-(Ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzonitrile (0.50 g, 1.70 mmol) in concentrated sulfuric acid (4 ml) is stirred at 100° C. for 1.5 h. After completion of 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-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide which is used in the next step without further purification (0.50 g, 1.60 mmol, 94%).

Workup

  1. customAfter completion of 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-d6314caf392f4db2bec4822f3cec23eb
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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