3-Chloropyridine → 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-chloro-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one

HRID 2292006Notes

Reaction equation

HRID 2292006 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]([Cl:16])([Cl:15])[CH2:10][O:11][C:12](Cl)=[O:13].[CH3:17][C:18]1[NH:19][C:20](=[O:24])[CH2:21][S:22][CH:23]=1>>[CH3:17][C:18]1[NH:19][C:20](=[O:24])[CH2:21][S:22][C:23]=1[CH:7]1[CH:6]=[CH:5][N:4]([C:12]([O:11][CH2:10][C:9]([Cl:16])([Cl:15])[Cl:8])=[O:13])[CH:3]=[C:2]1[Cl:1]

Participants

4

Reactant 3

HCID 122873-ChloropyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 136724195-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-chloro-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-oneYield 46.3%

Procedure

3-Chloropyridine (0.88 g), 2,2,2-trichloroethylchloroformate (1.33 ml) and 5-methyl-2H-1,4-thiazin-3(4H)-one (0.5 g) were treated in the same manner as described in Example 2 (i) to give the titled compound (0.75 g, yield 46.3%) as milky white crystals. Chloroform-methanol (=30:1) was used as a developing eluant.

Sources & evidence

ORD record
ord-aa3f4325837744c28cdfac4421ad5da7
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

Loading…