Toluene → N-{4-[(1,2-Benzothiazol-5-yl)oxy]phenyl}-N'-methylurea

HRID 280433Notes

Reaction equation

HRID 280433 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[S:14][N:13]=[CH:12][C:11]=3[CH:15]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[CH3:25][N:26]=[C:27]=[O:28]>C(N(CC)CC)C>[CH3:25][NH:26][C:27]([NH:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[S:14][N:13]=[CH:12][C:11]=3[CH:15]=2)=[CH:4][CH:3]=1)=[O:28]

Participants

5

Reactant 3

HCID 1140TolueneHCID 12228Methyl IsocyanateHCID 132693984-[(1,2-Benzothiazol-5-yl)oxy]aniline

Product 1

HCID 13269403N-{4-[(1,2-Benzothiazol-5-yl)oxy]phenyl}-N'-methylureaYield 85%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

24.2 parts of 5-(4'-aminophenoxy)-benzisothiazole, 400 parts of toluene, 1 part of triethylamine and 11.4 parts of methyl isocyanate were heated at 80° C. for 12 hours, and the reaction mixture was then evaporated down under reduced pressure. 25 parts (85% of theory) of 5-(4'-methylaminocarbonylaminophenoxy)-benzisothiazole of melting point 178° C. were obtained.

Workup

  1. customthe reaction mixture was then evaporated down under reduced pressure

Sources & evidence

ORD record
ord-5fe0223b8e87453fb76a6d3ed74252cd
Source dataset
uspto-grants-1986_05
Patent number
US04589910

Reaction notes

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