Pyridine → HCID 13518417, compound

HRID 2292025Notes

Reaction equation

[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[CH3:10][C:11]1[NH:12][C:13](=[O:17])[CH2:14][S:15][CH:16]=1.C(#N)C.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:10][C:11]1[NH:12][C:13](=[O:17])[CH2:14][S:15][C:16]=1[CH:24]1[CH:25]=[CH:26][N:21]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:22]=[CH:23]1

Participants

Reactant 4

HCID 1049Pyridine

HCID 6342Acetonitrile

HCID 870632,2,2-Trichloroethyl chloroformate

HCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 13518417HCID 13518417, compoundYield 80.7%

Procedure

2,2,2-Trichloroethylchloroformate (64 ml) was added dropwise to a suspension of 5-methyl-2H-1,4-thiazin-3(4H)-one (50 g) and acetonitrile (500 ml) in pyridine (75 ml) under ice/water-cooling. The reaction mixture was further stirred at ambient temperature for 1 hour. Then, the mixture was added with ice water (about 1.5 l), was stirred for a while and was filtered. The filtration was recrystallized from ethanol to give the titled compound (120 g, yield 80.7%) as pale yellow prisms.

Workup

temperaturecooling
stirringwas stirred for a while
filtrationwas filtered
filtrationThe filtration
customwas recrystallized from ethanol

Sources & evidence

ORD record: ord-ce020770cd104255bacfb8a568611a2d
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04800201

Reaction notes

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