Hydrochloric Acid → HCID 69360143, compound

HRID 852623Notes

Reaction equation

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

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of methyl 3-amino-5-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)benzoate (D267) (7.5 g, 26.4 mol, 1 equiv) in a 2N aqueous HCl solution (75 ml) and MeOH (75 ml) at 0° C. was added NaNO2 (4.0 g, 58.1 mmol, 2.2 equiv) portionwise over 20 min. MeOH (50 ml) and H2O (200 ml) were added and the resulting mixture was stirred at 95° C. for 1 h then cooled to room temperature. Most of the MeOH was removed in vacuo and the resulting aqueous phase was extracted with AcOEt. The insoluble material was filtered off to give methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-5-hydroxybenzoate (D) (0.63 g, 8%). The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give a brown residue which was redissolved in AcOEt. The organic phase was extracted with a saturated aqueous Na2CO3 solution and the aqueous phase was extracted three times with Et2O then acidified to pH 1 and re-extracted three times with AcOEt. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo to give methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-5-hydroxybenzoate (D268) (2.2 g, 30%).

Workup

temperaturethen cooled to room temperature
customMost of the MeOH was removed in vacuo
extractionthe resulting aqueous phase was extracted with AcOEt
filtrationThe insoluble material was filtered off

Sources & evidence

ORD record: ord-06f46216a92d40b4afeccb408d3037aa
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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