HCID 20144978, compound → HCID 20145027, compound

HRID 648596Notes

Reaction equation

HRID 648596 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][NH:8][C:9]1[S:10][C:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:12]([CH:14]=O)[N:13]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O>[CH3:7][NH:8][C:9]1[S:10][C:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:12]([CH:14]=[CH2:1])[N:13]=1

Participants

5

Reactant 2

HCID 20144978HCID 20144978, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20145027HCID 20145027, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert-butoxide (1.46 g) was added to a solution of 2-methylamino-5-(4-pyridyl)-4-thiazolecarbaldehyde (1.9 g) and methyltriphenylphosphonium bromide (4.66 g) in dimethyl sulfoxide (87 ml) and the mixture was stirred for 5 hours at ambient temperature. The reaction mixture was poured into ice-water (300 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with a saturated aqueous solution of sodium chloride (100 ml) and dried over magnesium sulfate. Solvent was distilled off and the residue was subjected to column chromatography on silica gel (120 g) and eluted with a mixture of chloroform and methanol (40:1). The fractions containing the object compound were combined and concentrated until the volume was about 15 ml. The resultant white needles were collected by filtration and washed with cold ethyl acetate and dried under reduced pressure to give white needles of 2-methylamino-5-(4-pyridyl)-4-vinylthiazole (510 mg).

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. distillationSolvent was distilled off
  5. washeluted with a mixture of chloroform and methanol (40:1)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated until the volume
  8. filtrationThe resultant white needles were collected by filtration
  9. washwashed with cold ethyl acetate
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-1082431640054c78b2700504828866f8
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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