Trifluoroacetic acid → 8-Chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

HRID 1059278Notes

Reaction equation

[Cl:1][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](COC)[C:7]=2[CH:19]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][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[NH:8][C:7]=2[CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into 250 ml of a solution of 26.9 g of 8-chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in methylene chloride was dropped 50 ml of trifluoroacetic acid at 0° C. After reacting at room temperature for 12 hours, the reaction mixture was cooled to 0° C. and neutralized by adding an aqueous solution of sodium hydrogencarbonate. The crystals thus precipitated were taken up by filtration and washed successively with water and diethyl ether to thereby give 19.1 g of the title compound as yellow crystals.

Workup

customThe crystals thus precipitated
filtrationwere taken up by filtration
washwashed successively with water and diethyl ether

Sources & evidence

ORD record: ord-a4fe67fb396c4809b613d57a387c8948
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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