Methyl iodide → 1-(6-Bromo-7-methoxy-2-benzothiazolyl)-3-ethyl-urea

HRID 9113Notes

Reaction equation

HRID 9113 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:18](=O)([O-])[O-].[K+].[K+].IC>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][CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219855951-(6-Bromo-7-hydroxy-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855201-(6-Bromo-7-methoxy-2-benzothiazolyl)-3-ethyl-ureaYield 2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6, potassium carbonate and iodomethane in DMF was reacted to give 0.0034 g (2%) of the desired compound 10. 1H NMR (DMSO) δ 10.88 (br s, 1H, NH), 7.55 (d, 1H, J=8.5 Hz, ArH), 7.33 (d, 1H, J=8.5 Hz, ArH), 6.82 (br s, 1H, NH), 3.93 (s, 3H, CH3), 3.18 (m, 2H, CH2), 1.09 (t, 3H, J=7.2 Hz, CH3); LC/MS 330 (MH+); RP-HPLC RT 3.04 minutes.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-12cf03b2e2304f0c877426f44e1029ac
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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