Dichloromethane → Methyl 4-(5-chloro-4-methylbenzothiazol-2-yl)allophanate

HRID 1438975Notes

Reaction equation

HRID 1438975 reaction equation
[CH3:1][O:2][C:3]([N:5]=[C:6]=[O:7])=[O:4].C(Cl)Cl.[NH2:11][C:12]1[S:13][C:14]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH3:22])[C:15]=2[N:16]=1>O1CCCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:14]2[S:13][C:12]([NH:11][C:6](=[O:7])[NH:5][C:3]([O:2][CH3:1])=[O:4])=[N:16][C:15]=2[C:17]=1[CH3:22]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 11804815-Chloro-4-methyl-1,3-benzothiazol-2-amineHCID 4156749Methyl isocyanatoformate

Product 1

HCID 21399912Methyl 4-(5-chloro-4-methylbenzothiazol-2-yl)allophanateYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 parts by weight of methoxycarbonylisocyanate in 15 parts by weight of methylene chloride was added gradually with stirring to a solution, at room temperature, of 4 parts by weight of 2-amino-5-chloro-4-methylbenzothiazole in 75 parts by weight of methylene chloride and 50 parts by weight of tetrahydrofuran. After stirring the reaction mixture at room temprature overnight, a product was isolated by filtration giving a 40% yield of methyl 4-(5-chloro-4-methylbenzothiazol-2-yl)allophanate having a melting point greater than 275° .

Workup

  1. customa product was isolated by filtration

Sources & evidence

ORD record
ord-bb8c8c72267340d39ef7c695b07815c1
Source dataset
uspto-grants-1977_11
Patent number
US04057638

Reaction notes

Loading…