Water → 4-Methoxy-7-(tetrahydro-pyran-2-yl)-benzothiazol-2-ylamine

HRID 1582163Notes

Reaction equation

COC(=O)[NH:4][C:5]1[S:6][C:7]2[C:13]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1.[OH-].[Na+].O>C(O)CO>[CH3:21][O:20][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[S:6][C:7]=2[C:13]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2.60 g (8.06 mmol) [4-methoxy-7-(tetrahydro-pyran-2-yl)-benzothiazol-2-yl]-carbamic acid methyl ester in 100 ml ethylene glycol was added 100 ml 2 N NaOH and the mixture was heated at 100° C. for 3 h. After cooling to room, the reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (acetone/hexane 1/4-1/2) afforded 1.70 g (80%) 4-methoxy-7-(tetrahydro-pyran-2-yl)-benzothiazol-2-ylamine as a white solid. ES-MS m/e (%): 265 (M+H+, 100).

Workup

temperatureAfter cooling to room
extractionextracted three times with dichloromethane
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9fa5ce414d914dee858df2343285f3b1
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734179B2

Reaction notes

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