Benzo(d)thiazol-2-amine → N-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl]-N'-(2-benzothiazolyl)urea

HRID 851792Notes

Reaction equation

HRID 851792 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[N:9]=[CH:10][NH:11][C:12]=1[CH3:13].[H-].[Na+].[C:16]([NH:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)(OCC)=[O:17].NC1SC2C=CC=CC=2N=1>N1C=CC=CC=1.CCCCC>[CH3:13][C:12]1[NH:11][CH:10]=[N:9][C:8]=1[CH2:7][S:6][CH2:5][CH2:4][NH:3][C:16]([NH:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)=[O:17]

Participants

7

Reactant 4

HCID 8706Benzo(d)thiazol-2-amineHCID 24758Sodium hydrideHCID 854169ethyl N-(1,3-benzothiazol-2-yl)carbamateHCID 30159992-(((5-Methyl-1H-imidazol-4-yl)methyl)thio)ethylamine dihydrochloride

Product 1

HCID 20501189N-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl]-N'-(2-benzothiazolyl)ureaYield 16.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8003PentaneSolvent

Procedure

The compound is prepared according to the method of Example 5 using 6.12 g (25.1 mmole) of 4-[(2-aminoethyl)thiomethyl]-5-methylimidazole dihydrochloride, and 2.29 g (50.2 mmole) of sodium hydride in oil in 100 ml of pyridine and 5.55 g (25.0 mmole) of 2-carbethoxyaminobenzothiazole, prepared from 2-aminobenzothiazole according to the method of Example 2. Chromatography, followed by trituration with pentane, affords the desired compound (1.43 g, 4.1 mmole). Structure assignment is supported by nmr.

Workup

  1. customThe compound is prepared

Sources & evidence

ORD record
ord-34aee4186345479cb065f9f92cf295d9
Source dataset
uspto-grants-1983_05
Patent number
US04386211

Reaction notes

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