Sodium Iodide → methyl 3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

HRID 2421841Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][CH2:13][CH2:14]Cl)[C:5]([O:7][CH3:8])=[O:6].[I-].[Na+]>CC(=O)CC>[S:12]1[CH2:13][CH2:14][NH:1][C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]1=2

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 3-amino-4-(2-chloroethylthio)benzoate (19.7 mg, 0.080 mmol) in 2-butanone (2 mL) was added sodium iodide (36 mg, 0.240 mmol). The reaction mixture was heated to 70° C. and stirred over night at that temperature. The reaction mixture was cooled to room temperature. TLC and LCMS analysis of the reaction mixture indicated product formation. The product was purified by flash column chromatography [gradient elution with Hexanes and 5-50% EtOAc]. To provide methyl 3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate (8.6 mg, 0.040 mmol, 49.6% overall 3 steps) as an off-white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe product was purified by flash column chromatography [gradient elution with Hexanes and 5-50% EtOAc]

Sources & evidence

ORD record: ord-0f41cda3d215439eb7ce5f920d4b2fb0
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960376B2

Reaction notes

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