Hydrochloric Acid → HCID 21277737, compound

HRID 2292032Notes

Reaction equation

HRID 2292032 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Cl:6]C1C=C(C=CC=1)C(O[CH:13]1[C:18](=[O:19])[NH:17][C:16]([CH3:20])=[C:15]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[S:14]1)=O.Cl>ClCCl.CO>[ClH:6].[CH2:1]([N:3]([CH2:4][CH3:5])[CH:13]1[C:18](=[O:19])[NH:17][C:16]([CH3:20])=[C:15]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[S:14]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 139360302-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one

Product 1

HCID 21277737HCID 21277737, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Diethylamine (2.58 ml) was added to a solution of 2-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (0.9 g) in dry dichloromethane (12 ml) and the mixture was stirred at ambient temperature for 21 hours. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, was washed with saturated sodium bicarbonate aqueous solution and successively with water and was dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel (Wakogel C-200) column, using chloroform-methanol (=20:1) as an eluant to give pale yellow oily product. The oily product was dissolved in methanol and was adjusted to pH 2 by 2N hydrochloric acid. The solvent was removed under reduced pressure and the residue was washed with THF and allowed to stand to give the titled compound (0.685 g, yield 78.4%) as yellow crystals.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwas washed with saturated sodium bicarbonate aqueous solution and successively with water
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed on silica gel (Wakogel C-200) column
  7. customto give pale yellow oily product
  8. customThe solvent was removed under reduced pressure
  9. washthe residue was washed with THF

Sources & evidence

ORD record
ord-665219d8b54d4113a766b1a18d4affb6
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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