Hydrochloric Acid → HCID 54160621, compound

HRID 1906014Notes

Reaction equation

HRID 1906014 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=O)[N:7]=1.Cl.[I-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1.O>[CH3:1][NH:2][C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=[CH:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 20144978HCID 20144978, compoundHCID 86741343HCID 86741343, compound

Product 1

HCID 54160621HCID 54160621, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methylamino-4-formyl-5-(4-pyridyl)thiazole (1.1 g) in a mixture of tetrahydrofuran (40 ml) and water (40 ml) was added triphenyl (4-pyridylmethyl)phosphonium iodide hydrochloride (7.8 g). The resultant mixture was stirred at ambient temperature for 3 hours, during which time the mixture was maintained at pH 9.5 to 10 with 20% aqueous potassium carbonate. The reaction mixture was adjusted to pH 1.0 with 10% hydrochloric acid and washed with ethyl acetate. The aqueous solution was adjusted to pH 7.0 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The organic extract was dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and tetrahydrofuran (4:1). The fractions containing the desired compound were combined and evaporated in vacuo to give 2-methylamino-4-[2-(4-pyridyl)vinyl]-5-(4-pyridyl)thiazole (0.16 g).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and tetrahydrofuran (4:1)
  7. additionThe fractions containing the desired compound
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-eedc580e150d41f0b54af53b196ae7ea
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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