Dichloromethane → 4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate

HRID 742125Notes

Reaction equation

HRID 742125 reaction equation
[OH:1][CH2:2][C:3]1[S:7][CH:6]=[N:5][CH:4]=1.C(Cl)Cl.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:13]>C(Cl)(Cl)Cl>[CH:19]1[C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=[C:15]([O:14][C:12]([O:1][CH2:2][C:3]2[S:7][CH:6]=[N:5][CH:4]=2)=[O:13])[CH:20]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 821294-Nitrophenyl chloroformateHCID 27632165-Thiazolylmethanol

Product 1

HCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.11 g (27 mmol) of 5-(hydroxymethyl)thiazole and excess N-methyl morphcline in 1 DO ml of methylene chloride was cooled to 0° C. and treated with 8.2 g (41 mmol) of 4-nitrophenyl chloroformate. After being stirred for 1 h, the reaction mixture was diluted with CHCl3, washed successively with 1N HCl, saturated aqueous NaHCO3, and saturated brine, dried over NaSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (SIO2, 1-2% MeOH/CHCl3, Rf=0.5 in 4% MeOH/CHCl3) to yield 5.9 g (78%) of the desired compound as a yellow solid. NMR (CDCl3) δ5.53 (s, 2H), 7.39 (dt, J=9, 3 Hz, 2H), 8.01 (s, 1H), 8.29 (dr, J=9, 3 Hz, 2H), 8.90 (s, 1H). Mass spectrum: (M+H)+ =281.

Workup

  1. washwashed successively with 1N HCl, saturated aqueous NaHCO3, and saturated brine
  2. dry with materialdried over NaSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (SIO2, 1-2% MeOH/CHCl3, Rf=0.5 in 4% MeOH/CHCl3)

Sources & evidence

ORD record
ord-5324f8a700714ad0a05bc1dd48d68147
Source dataset
uspto-grants-1996_09
Patent number
US05552558

Reaction notes

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