4-Methylthiazole → HCID 23154591, compound

HRID 2244113Notes

Reaction equation

HRID 2244113 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][C:17](N(OC)C)=[O:18])=[CH:15][C:10]=2[O:9][CH2:8]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][C:17]([C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)=[O:18])=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

6

Reactant 3

HCID 127484-MethylthiazoleHCID 25517Ammonium ChlorideHCID 149181612-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methylacetamide

Product 1

HCID 23154591HCID 23154591, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A 2.6M solution of n-butylithium in hexane (34 ml) was dropped into a solution of 4-methylthiazole (8.0 g) of tetrahydrofuran (150 ml) at −70° C. and the mixture was stirred for 30 minutes. Further, a solution of 2-benzo(1,3)dioxol-5-yl-N-methoxy-N-methylacetamide (20.0 g) in tetrahydrofuran (20 ml) was dropped therein and the mixture was stirred for 1 hour. This solution, to which a saturated aqueous solution of ammonium chloride was added, was extracted with ethyl acetate, and after the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated. The resultant residue was purified by silica gel flash column chromatography using a mixed solvent of ethyl acetate and hexane to yield 2-benzo(1,3)dioxol-5-yl-1-(4-methylthiazol-2-yl)ethanone (19.3 g).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. dry with materialafter the organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe resultant residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-a4af4b97172f4577bbe41f5b7c45df80
Source dataset
uspto-grants-2010_03
Patent number
US07678810B2

Reaction notes

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