Methanol → HCID 23716256, compound

HRID 1059440Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.CO.[S:22]([O-:25])([O-:24])=[O:23].[Na+:26].[Na+]>O.C(O)C>[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH2:2][S:22]([O-:25])(=[O:24])=[O:23])[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2.[Na+:26]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 900 mg of 8-chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in a mixture of water (8 ml)/methanol (4 ml) was added 0.8 g of sodium sulfite and the resulting mixture was heated to 90° C. for 2 hours. Then the reaction mixture was brought back to room temperature and diluted with ethanol. After filtering off the inorganic salt, silica gel was added to the filtrate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/acetic acid) to thereby give 650 mg of the title compound as yellow crystals.

Workup

customwas brought back to room temperature
filtrationAfter filtering off the inorganic salt, silica gel
additionwas added to the filtrate
distillationAfter distilling off the solvent under reduced pressure
customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/acetic acid)

Sources & evidence

ORD record: ord-4909978d783342c3a949339be3eca397
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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