2-Nitro-1-phenylethanone → 2-nitro-1-phenyl-2-(tetrahydro-2H-1,3-thiazin-2-ylidene)ethanone

HRID 597743

Reaction equation

HRID 597743 reaction equation
[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])([O-:3])=[O:2].CS[C:15]1[S:16][CH2:17][CH2:18][CH2:19][N:20]=1>[Cl-].[Zn+2].[Cl-]>[N+:1]([C:4](=[C:15]1[NH:20][CH2:19][CH2:18][CH2:17][S:16]1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 948332-Nitro-1-phenylethanoneHCID 27820812-(methylsulfanyl)-5,6-dihydro-4H-1,3-thiazine

Product 1

HCID 731795232-nitro-1-phenyl-2-(tetrahydro-2H-1,3-thiazin-2-ylidene)ethanone

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 3.3 g of 2-nitroacetophenone and 2.94 g of 2-(methylthio)-5,6-dihydro-4H-1,3-thiazine was heated to 115° and 100 milligrams of zinc chloride was added. Heating and stirring was continued at 115°-120° for 2.5 hours. After cooling, the mixture was filtered (with the aid of ethyl acetate) through a short column of florosil to give an amber oil. The oil was chromatographed on silica gel using dry-column technique and a 1:1:2 mixture of tetrahydrofuran/ethyl acetate/hexane for development to give 1 as a salmon-colored solid, m.p.: 137°-140°.

Workup

  1. temperaturewas heated to 115°
  2. temperatureHeating
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered (with the aid of ethyl acetate) through a short column of florosil
  5. customto give an amber oil
  6. customThe oil was chromatographed on silica gel using dry-column technique
  7. additiona 1:1:2 mixture of tetrahydrofuran/ethyl acetate/hexane for development

Sources & evidence

ORD record
ord-20571468b470489bb650b0aac4f087c5
Source dataset
uspto-grants-1977_03
Patent number
US04015001

Linked notes

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