Methanol → 1-Benzothiazol-6-yl-3-(2-chloro-1,1-dimethyl-ethyl)-urea

HRID 80214

Reaction equation

HRID 80214 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:11][CH2:12][C:13]([N:16]=[C:17]=[O:18])([CH3:15])[CH3:14].CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:17]([NH:16][C:13]([CH3:15])([CH3:14])[CH2:12][Cl:11])=[O:18])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 682886-AminobenzothiazoleHCID 110407471-Chloro-2-isocyanato-2-methyl-propane

Product 1

HCID 687898531-Benzothiazol-6-yl-3-(2-chloro-1,1-dimethyl-ethyl)-ureaYield 18.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

Benzothiazol-6-ylamine (1.8 g, 12.00 mmol) was added portion wise to solution of 1-chloro-2-isocyanato-2-methyl-propane (2 g, 13.60 mmol) in toluene (20 mL) over a period of 5 minutes. The resulting mixture was stirred at room temperature for 2½ days. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was concentrated and extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 630 mg of the product (16.57% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethylacetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

Sources & evidence

ORD record
ord-7d4430f7215241d5bbc8a1235cd54f54
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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