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

HRID 1781086Notes

Reaction equation

HRID 1781086 reaction equation
[OH:1][CH2:2][C:3]1[S:7][CH:6]=[N:5][CH:4]=1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:16]1[C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=[C:12]([O:11][C:9]([O:1][CH2:2][C:3]2[S:7][CH:6]=[N:5][CH:4]=2)=[O:10])[CH:17]=1

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 27632165-Thiazolylmethanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.11 g (27 mmol) of 5-(hydroxymethyl)thiazole and excess N-methyl morphcline in 100 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 (dt, 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-62b01f02baa24502b500f023bdca3e5a
Source dataset
uspto-grants-1997_05
Patent number
US05631376

Reaction notes

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