Methanol → HCID 66660824, compound

HRID 556703Notes

Reaction equation

HRID 556703 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[S:18][CH:17]=[N:16][C:15]=2[CH3:19])(=O)=[O:9])=CC=1.[NH2:20][C:21]1[S:22][C:23]([CH3:26])=[CH:24][N:25]=1.CO>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(Cl)Cl>[OH-:9].[NH4+:16].[CH3:26][C:23]1[S:22][C:21](=[NH:20])[N:25]([CH2:12][CH2:13][C:14]2[S:18][CH:17]=[N:16][C:15]=2[CH3:19])[CH:24]=1

Participants

8

Reactant 3

HCID 887MethanolHCID 3517702-Amino-5-methylthiazoleHCID 7303349HCID 7303349, compound

Product 2

HCID 14923Ammonium HydroxideHCID 66660824HCID 66660824, compoundYield 102.8%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
85 °C

Procedure

A mixture of 2-(4-methylthiazol-5-yl)ethyl 4-methylbenzenesulfonate (3.23 g, 10.9 mmol), 2-amino-5-methylthiazole (1.25 g, 10.9 mmol) and tetrabutyl ammonium iodide (2 g, 5.4 mmol) in N,N-dimethylformamide (2 mL) was warmed to 85° C. and was stirred for 18 h. The mixture was cooled to ambient temperature, was diluted with CH2Cl2 (10 mL) and was quenched with 10% NaOH (5 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 10% methanol in ethyl acetate then 9:1:0.1 CH2Cl2:methanol:ammonium hydroxide) to give the title compound (1.34 g, 5.6 mmol, 51% yield). MS (DCI/NH3) m/z 240 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customwas quenched with 10% NaOH (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×5 mL)
  5. dry with materialThe combined organics were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified via column chromatography (SiO2, 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-e8aa9f6d82724d56a8f254798b361d51
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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