Benzenethiol, 2-amino-, hydrochloride (1:1) → Ethyl 2-[4-(benzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

HRID 1655894Notes

Reaction equation

[C:1]([CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]1=[O:20])#[N:2].Cl.N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29]>O>[S:29]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:2]=[C:1]1[CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]1=[O:20]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 208 mg of ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate and 116 mg of 2-aminothiophenol hydrochloride was heated at 180° C. for 15 minutes to fuse them. After the mixture had been cooled, water was added, and then extracted with ethyl acetate. After the drying of the organic layer over anhydrous magnesium sulfate, the solvent was distilled off. The resulting oily matter was purified by silica gel chromatography to give 196 mg of the title compound. The structural formula and physical data of this compound are shown in Table 15.

Workup

temperatureAfter the mixture had been cooled
extractionextracted with ethyl acetate
dry with materialAfter the drying of the organic layer over anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe resulting oily matter was purified by silica gel chromatography

Sources & evidence

ORD record: ord-c897ccbf25c14139924b6ecfb0f78c98
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252571

Reaction notes

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