Hydrochloric Acid → HCID 22990015, compound

HRID 1169479Notes

Reaction equation

HRID 1169479 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH3:32])[O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:15](=[O:17])(=[O:16])[CH2:14][CH2:13][C:12]([C:18]([O:20]C)=[O:19])=[CH:11][C:10]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl>O1CCCC1.CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH3:32])[O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:15](=[O:16])(=[O:17])[CH2:14][CH2:13][C:12]([C:18]([OH:20])=[O:19])=[CH:11][C:10]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 22989978HCID 22989978, compound

Product 1

HCID 22990015HCID 22990015, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Into a mixed solution of methyl 7-[3-methyl-4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (470 mg) in tetrahydrofuran (10 ml) and methanol (5 ml) was added a 1 N aqueous solution of potassium carbonate (2.9 ml), and the resulting mixture was heated at 65° C. for one day. After cooling, the reaction mixture was mixed with water, was acidified (pH=4) with 1N hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 7-[3-methyl-4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (375 mg) as a brown oily substance.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3a60a5ae71f341c6a4f3e6e5a77159eb
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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