1,3-Dichloroacetone → tert-Butyl (4-(chloromethyl)thiazol-2-yl)carbamate

HRID 1020243Notes

Reaction equation

HRID 1020243 reaction equation
[C:1]([NH:8][C:9]([NH2:11])=[S:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.C([O-])(O)=O.[Na+].CCOC(C)=O.CCCCCCC>CC(C)=O>[C:1]([NH:8][C:9]1[S:10][CH:16]=[C:14]([CH2:13][Cl:12])[N:11]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 4095660N-Boc thioureaHCID 21899848Ethylacetate heptane

Product 1

HCID 45117840tert-Butyl (4-(chloromethyl)thiazol-2-yl)carbamateYield 68.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of Intermediate VII (3.0 g, 17 mmol) in acetone (75 mL) was added 1,3-dichloroacetone (2.4 g, 18.7 mmol) at once. The mixture was stirred at room temperature for 72 h. The reaction mixture was treated with NaHCO3 (3 g) and stirred for 15 min. The solids were removed by filtration and the filtrate was concentrated in vacuo. Column chromatography (EtOAc/Heptane, 4/1) afforded N-Boc-4-(chloromethyl)thiazol-2-amine (2.9 g, 11.6 mmol, 68%) as a white solid.

Workup

  1. stirringstirred for 15 min
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d3db53d551964a488dfa56dd2717c2ff
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

Loading…