Ammonia → HCID 86699767, compound

HRID 515202Notes

Reaction equation

HRID 515202 reaction equation
[CH:1]([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]([O:18][CH3:19])[C:5]=1[C:6]#[N:7])([CH3:3])[CH3:2].N.S(=O)(=O)(O)[OH:22]>>[CH:1]([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]([O:18][CH3:19])[C:5]=1[C:6]([NH2:7])=[O:22])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 86699766HCID 86699766, compound

Product 1

HCID 86699767HCID 86699767, compoundYield 86%

Procedure

A solution of 2-isopropyl-6-methoxy-4-morpholin-4-yl-benzonitrile (0.37 g, 1.42 mmol) in sulfuric acid (20 ml) is heated at 100° C. for 3 h. After completion of the reaction (monitored by TLC), the mixture is poured onto ice water. The aqueous layer is basified with aqueous ammonia to pH 10 and extracted with ethyl acetate (3×20 ml). The combined organic layers are washed with water (10 ml), dried over sodium sulfate and concentrated in vacuo yielding 2-isopropyl-6-methoxy-4-morpholin-4-yl-benzamide (0.34 g, 1.22 mmol, 86%).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. additionthe mixture is poured onto ice water
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined organic layers are washed with water (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e42dbf22ee3d4d7ab5865df3c086d6ab
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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