2-Bromopropane → 1-(6-Bromo-7-isopropoxy-2-benzothiazolyl)-3-ethylurea

HRID 9114

Reaction equation

HRID 9114 reaction equation
[Br:1][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+].Br[CH:25]([CH3:27])[CH3:26]>CN(C=O)C>[Br:1][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[O:17][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 219855951-(6-Bromo-7-hydroxy-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855461-(6-Bromo-7-isopropoxy-2-benzothiazolyl)-3-ethylureaYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6, potassium carbonate and 2-bromopropane in DMF was reacted to give 0.046 g (81%) of the desired compound 11. 1H NMR (DMSO) δ 10.83 (br s, 1H, NH), 7.55 (d, 1H, J=8.5 Hz, ArH), 7.31 (d, 1H, J=8.6 Hz, ArH), 6.71 (br s, 1H, NH), 4.69 (hept, 1H, J=6.0 Hz, CH), 3.18 (m, 2H, CH2), 1.32 (d, 6H, J=6.1 Hz, CH3), 1.09 (t, 3H, J=7.2 Hz, CH3); LC/MS 358 (MH+); RP-HPLC RT 3.42 minutes.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-a370cc9a12cf48bda09d8ac2cf6359f2
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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