Methanol → 1-(7-Hydroxy-2-benzothiazolyl)-3-ethyl-urea

HRID 9111

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

General Procedure for 1-(6-bromo-7-alkoxy-2-benzothiazolyl)-3-ethyl-urea compounds 9–13. A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 and potassium carbonate (1.05 eq) in anhydrous DMF was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The mixture was treated with an alkyl halide (1.0 eq), and was stirred at about 0–85° C. for about 16 hours. To the reaction mixture was added methanol. The solid was filtered off and washed with methanol. The solvent was evaporated and the residue was dissolved in DMF. The crude reaction solution was purified by preparature LC/MS to give pure desired product.

Workup

temperaturewas cooled down to about 0° C
stirringwas stirred at about 0–85° C. for about 16 hours
filtrationThe solid was filtered off
washwashed with methanol
customThe solvent was evaporated
dissolutionthe residue was dissolved in DMF
customThe crude reaction solution
customwas purified by preparature LC/MS

Sources & evidence

ORD record: ord-b7720941bb934e35991fd79ffdaedd76
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Linked notes

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