Sodium Hydroxide → (+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine

HRID 985786Notes

Reaction equation

COC(=O)[NH:4][C:5]1[S:6][C:7]2[C:13]([CH:14]3[CH2:19][O: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+]>O1CCOCC1.C(O)CO>[O:15]1[CH2:16][CH2:17][O:18][CH2:19][CH:14]1[C:13]1[C:7]2[S:6][C:5]([NH2:4])=[N:9][C:8]=2[C:10]([O:20][CH3:21])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 1.10 g (3.39 mmol) (±)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 50 ml dioxane and 50 ml ethylene glycol was added 100 ml of a 5 N aq. sodium hydroxide solution and the mixture was heated at 100° C. for 16 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with brine, then dried over sodium sulfate and concentrated in vacuo. Trituration in methanol afforded 0.66 g (73%) (±)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine as a white solid. ES-MS m/e (%): 267 (M+H+, 100).

Workup

temperatureAfter cooling to room temperature the mixture
additionwas poured onto water
extractionextracted three times with ethyl acetate
washThe combined organic phases were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-10f8e0df4f8b41ffbbbe829e31ab5233
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872833B2

Reaction notes

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