Dimethylamine → 6-Ethoxycarbonyl-2-dimethylaminomethylbenzothiazole

HRID 465043Notes

Reaction equation

HRID 465043 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].C1[C:21](=O)[N:20](Br)[C:18](=O)C1.CNC>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH2:13][N:20]([CH3:21])[CH3:18])[S:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 67184N-bromobutanimideHCID 640775Ethyl 2-methyl-1,3-benzothiazole-6-carboxylate

Product 1

HCID 202616576-Ethoxycarbonyl-2-dimethylaminomethylbenzothiazoleYield 32%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6-ethoxycarbonyl-2-methylbenzothiazole (2.09 g) prepared according to the method described in J. Gen. Chem. vol. 5, pp. 260-266 (1945) was subjected to bromination with NBS (1.78 g) in carbon tetrachloride (30 mg). Then, the product was caused to react with dimethylamine to yield a new compound of 6-ethoxycarbonyl-2-dimethylaminomethylbenzothiazole (0.8 g). Then, the compound was provided with the same treatment as that described in Examples 49-51 to yield 6-[(2-aminoethyl)thiomethyl]-2-(dimethylaminomethyl)benzothiazole.2hydrobromide (1.2 g).

Sources & evidence

ORD record
ord-e5b996a123ce4f00ab642a722feae493
Source dataset
uspto-grants-1985_10
Patent number
US04550118

Reaction notes

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