2,2,2-Trichloroethyl chloroformate → HCID 15908473, compound

HRID 480027Notes

Reaction equation

HRID 480027 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][CH2:11][N:12]1[C:17]2[CH2:18][CH2:19][S:20][CH2:21][C:16]=2[C:15](=[O:22])[NH:14][C:13]1=[O:23])C1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27]>C(#N)C>[O:23]=[C:13]1[N:12]([CH2:11][CH2:10][CH2:9][N:8]([CH3:1])[C:26](=[O:27])[O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])[C:17]2[CH2:18][CH2:19][S:20][CH2:21][C:16]=2[C:15](=[O:22])[NH:14]1

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 18768327HCID 18768327, compound

Product 1

HCID 15908473HCID 15908473, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 11.5 g (33.29 mmol) of 1-{3-[benzyl(methyl)amino]propyl}-1,5,7,8-tetrahydro-2H-thiopyrano[4,3-d]pyrimidine-2,4-(3H)-dione in 200 ml of acetonitrile is treated with 7.92 g (36.63 mmol) of 2,2,2-trichloroethyl chloroformate, and the mixture is stirred at room temperature for 30 minutes. The solvent is then removed under reduced pressure and the residue is purified by column chromatography (silica gel, cyclohexane/ethyl acetate 1:1). This gives 9.4 g (63% yield) of a colourless solid.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customthe residue is purified by column chromatography (silica gel, cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-c27bd444482649f3a41478e10f58ed72
Source dataset
uspto-grants-2003_11
Patent number
US06649618B2

Reaction notes

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