Hydrochloric Acid → HCID 54475154, compound

HRID 371082Notes

Reaction equation

HRID 371082 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N+:6]([CH:9]=[C:10]1[NH:15][CH2:14][CH2:13][CH2:12][S:11]1)([O-:8])=[O:7].C(N(CC)CC)C.Cl>CN(C)C=O>[C:1]([N:15]1[CH2:14][CH2:13][CH2:12][S:11][C:10]1=[CH:9][N+:6]([O-:8])=[O:7])(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineHCID 62324Propionyl chloride

Product 1

HCID 54475154HCID 54475154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-25 °C

Procedure

Propionyl chloride (1.8 g) was added dropwise over a period of 15 minutes to a mixture of 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (2.0 g) and triethylamine (2.4 g) in dimethylformamide (8 ml) at -30° C. under nitrogen. The reaction mixture was stirred for a further period of 35 minutes at -25° C. and was then poured into 2% hydrochloric acid. The mixture was extracted with dichloromethane and the organic layer was washed with sodium chloride solution and dried (Na2SO4). The solvent was then removed under reduced pressure and the residue was purified by chromatography on silica gel using 1% methanol in dichloromethane as eluent to yield the required product as a yellow crystalline solid m.p. 84°-86° C.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe organic layer was washed with sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was then removed under reduced pressure
  5. customthe residue was purified by chromatography on silica gel using 1% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-77fa30c1de894b7c80e17b435ac731f5
Source dataset
uspto-grants-1985_07
Patent number
US04529726

Reaction notes

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