Sulfuric Acid → HCID 21995945, compound

HRID 1978676Notes

Reaction equation

HRID 1978676 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][C:17]([C:23]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]([CH3:40])[CH:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[CH:28][CH:27]=4)=[O:24])=[CH:16][C:15]=3[CH:41]=2)=[CH:7][CH:6]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C1COCC1.CC(C)=O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][C:17]([C:23]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]([CH3:40])[CH:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[CH:28][CH:27]=4)=[O:24])=[CH:16][C:15]=3[CH:41]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 21995886HCID 21995886, compound

Product 1

HCID 21995945HCID 21995945, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 22559816Acetone tetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

In THF/acetone (1/1, 60 ml) was dissolved 7-(4-methoxymethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (650 mg). To the mixture was added 1N sulfuric acid (4.4 ml), and the mixture was stirred at 65° C. for 14 hours, cooled to room temperature and neutralized with saturated sodium bicarbonate solution. Under reduced pressure, the solvent was evaporated, and the residue was added to water. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethanol to give 7-(4-hydroxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 89) (530 mg).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionthe residue was added to water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-00c2140a485a4458ae2ce5a10c697a12
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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