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

HRID 1685018Notes

Reaction equation

HRID 1685018 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+]>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

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 4095660N-Boc thiourea

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-Boc-thiourea (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 3 g of NaHCO3 and stirred for 15 min. The solids were removed by filtration and the filtrate was concentrated in vacuo. Column chromatography (EtOAc/Heptanes 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-c2ac4b517c1941708f18ba4abfb8e6d8
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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