Ethyl Acetate → HCID 18953902, compound

HRID 2379872Notes

Reaction equation

HRID 2379872 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH2:22][C:23](=[N:25][C:26]1[S:27][CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][OH:38])[N:32]=2)[N:30]=1)[NH2:24].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1>[NH2:24][C:23](=[N:25][C:26]1[S:27][CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[O:38])[N:32]=2)[N:30]=1)[NH2:22]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2724130Cornforth reagentHCID 18953921HCID 18953921, compound

Product 1

HCID 18953902HCID 18953902, compoundYield 18.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pyridinium dichromate (3.2 g) in N,N-dimethylformamide (10 ml) was added dropwise to a solution of 2-(diaminomethyleneamino)-4-(6-hydroxymethylpyridin-2-yl)thiazole (1.7 g) in N,N-dimethylformamide (17 ml) at -10~-5° C. and the mixture was stirred for 5 hours at the same temperature. The reaction mixture was added to a mixture of ethyl acetate, tetrahydrofuran and water and the mixture was adjusted to pH 10 with potassium carbonate. The separated organic layer was washed with brine, and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-(diaminomethyleneamino)-4-(6-formylpyridin-2-yl)thiazole (0.31 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of a solvent
  4. customgave a residue, which
  5. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V)
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-eba208b894f64039892f109cb9890788
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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