Hydrochloric Acid → HCID 86699754, compound

HRID 515187Notes

Reaction equation

HRID 515187 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([CH3:17])[C:4]=1[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].C(S)C.Cl>CN(C)C=O.O>[OH:2][C:3]1[CH:10]=[C:9]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:8]=[C:7]([CH3:17])[C:4]=1[C:5]#[N:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 86699753HCID 86699753, compound

Product 1

HCID 86699754HCID 86699754, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-methoxy-6-methyl-4-morpholin-4-yl-benzonitrile (0.9 g, 3.88 mmol) in dimethylformamide (15 ml) are added potassium carbonate (2.1 g, 15.5 mmol) and ethanethiol (2.3 ml, 31.0 mmol) and the resulting mixture is heated at 90° C. for 16 h. The reaction mixture is poured onto cold water (50 ml), acidified with 2M hydrochloric acid to pH 3 and extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude product is purified by flash column chromatography (silica gel, 30% ethyl acetate/hexane) affording 2-hydroxy-6-methyl-4-morpholin-4-yl-benzonitrile (0.41 g, 1.88 mmol, 48%).

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washThe combined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by flash column chromatography (silica gel, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-25b13ddcc8d1455d961a7a79e4a9a82a
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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