Dimethylcarbamoyl Chloride → Urea, 3-(2-benzothiazolyl)-1,1-dimethyl-

HRID 2052205Notes

Reaction equation

HRID 2052205 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][N:12]([CH3:16])[C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClC=C(Cl)Cl>[CH3:11][N:12]([CH3:16])[C:13]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)=[O:14]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8706Benzo(d)thiazol-2-amineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 99155Urea, 3-(2-benzothiazolyl)-1,1-dimethyl-Yield 97.7%

Reagents, catalysts & solvents 1

HCID 6575TrichloroethyleneSolvent

Procedure

Using 2-aminobenzothiazole (1.50 g), N,N-dimethylcarbamoyl chloride (1.29 g), aluminum chloride (1.60 g), and trichloroethylene (40 ml), the reaction is effected as in Example 1, except that the reflux is carried out for 40 hours. Thus, 1,1-dimethyl-3-(2-benzothiazolyl)urea (2.16 g) is obtained. Yield is 97.7%. Melting point is higher than 300° C. (after recrystallization from ethanol).

Sources & evidence

ORD record
ord-b1da622f11aa4dbd85fc654d4a51ced1
Source dataset
uspto-grants-1980_01
Patent number
US04183856

Reaction notes

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