Hydrochloric Acid → 1-(Morpholin-2-ylmethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide hydrochloride

HRID 1818776Notes

Reaction equation

[O:1]=[S:2]1(=[O:31])[N:6]([CH2:7][CH:8]2[O:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)[C:5]2[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=2[N:3]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[ClH:32]>CO>[ClH:32].[NH:10]1[CH2:11][CH2:12][O:13][CH:8]([CH2:7][N:6]2[C:5]3[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=3[N:3]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[S:2]2(=[O:31])=[O:1])[CH2:9]1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of tert-butyl 2-[(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)methyl]morpholine-4-carboxylate (385 mg, 0.864 mmol) in methanol (5 mL) was added slowly an ethereal solution of hydrochloric acid (1M, 10 mL). The mixture was swirled for 20 minutes. All volatiles were removed under reduced pressure. The white precipitate was redissolved in minutesimal amount of methanol (˜1 mL). Isopropyl ether was added until the solution became slightly cloudy. The mixture was cooled to −30° C. in a freezer. The white solid formed was collected by decantation, washed with hexane and dried in vacuo to give 327 mg (99%) of 1-(morpholin-2-ylmethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide hydrochloride as a white powder. MS (ESI) m/z 345.9 ([M+H]+).

Workup

customAll volatiles were removed under reduced pressure
dissolutionThe white precipitate was redissolved in minutesimal amount of methanol (˜1 mL)
additionIsopropyl ether was added until the solution
customThe white solid formed
customwas collected by decantation
washwashed with hexane
customdried in vacuo

Sources & evidence

ORD record: ord-6d3076043e814da49335c630f3838783
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601722B2

Reaction notes

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