Dimethylformamide → HCID 20270257, compound

HRID 1075009Notes

Reaction equation

HRID 1075009 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:19]=1.[CH3:20]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].CI>O>[CH3:20][O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20270234HCID 20270234, compound

Product 1

HCID 20270257HCID 20270257, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 G. 8-hydroxydibenzo[b,f]thiepin-3-carboxylic acid is stirred in 50 cc. dimethylformamide with 1.5 g. potassium carbonate and 3 cc. methyl iodide. 100 cc. water is added to the reaction mixture, heated for three hours and then extracted with ethyl acetate, and the aqueous layer acidified. The precipitated solid is filtered, washed with water and a small volume of cold methanol, and dried. Yield of the desired material 700 mg.

Workup

  1. temperatureheated for three hours
  2. extractionextracted with ethyl acetate
  3. filtrationThe precipitated solid is filtered
  4. washwashed with water
  5. dry with materiala small volume of cold methanol, and dried

Sources & evidence

ORD record
ord-fbc05f44ee7c45f2a04083854c27ea6c
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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