Sulfuric Acid → 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide

HRID 515148Notes

Reaction equation

HRID 515148 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([S:8][C:9]1[CH:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C@H:18]2[CH3:23])[CH:14]=[C:13]([CH3:24])[C:10]=1[C:11]#[N:12])[CH3:7]>>[CH2:6]([S:8][C:9]1[CH:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C@H:18]2[CH3:23])[CH:14]=[C:13]([CH3:24])[C:10]=1[C:11]([NH2:12])=[O:2])[CH3:7]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86699725HCID 86699725, compound

Product 1

HCID 866997262-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide

Conditions

Temperature
100 °C

Procedure

Concentrated sulfuric acid (5 ml) is added to 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzonitrile (0.11 g, 0.40 mmol) at RT and the resulting mixture is heated at 100° C. for 4 h. Upon completion (monitored by TLC), the reaction is slowly quenched with ice at 0° C. The mixture is basified with aqueous ammonia (pH=10). The aqueous part is extracted with ethyl acetate (3×10 ml). The combined organic layers are washed with water (10 ml), brine (10 ml), dried over anhydrous sodium sulfate and evaporated to get 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide which is used in the next step without further purification (0.075 g, 0.26 mmol, 55%).

Workup

  1. customUpon completion (monitored by TLC), the reaction is slowly quenched with ice at 0° C
  2. extractionThe aqueous part is extracted with ethyl acetate (3×10 ml)
  3. washThe combined organic layers are washed with water (10 ml), brine (10 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4b4e5bc1496945fb8273814ef70aaef3
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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