Water → HCID 1481569, compound

HRID 2174178Notes

Reaction equation

HRID 2174178 reaction equation
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][CH:7]=1)=[O:5].[CH3:18][Mg]Br.O>C1COCC1.C(OCC)C>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]2[S:10][C:6]([C:4](=[O:5])[CH3:18])=[CH:7][N:8]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 89312411HCID 89312411, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 1481569HCID 1481569, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-methoxy-N-methyl-2-(3-pyridyl)thiazole-5-carboxamide (5.6 g, 21.9 mmol) in 150 ml of THF was cooled to 0° C. and treated with methyl magnesium bromide (8.4 ml of a 3M solution in diethyl ether, 24.1 mmol). The reaction was stirred at 0° C. and shown to be complete by LC/MS and TLC after 1 Hr. The mixture was hydrolyzed with 5 ml water and evaporated. The residue was taken up in 200 ml of ethyl acetate and washed with 2×80 ml water and 1×80 ml brine. The organic phase were dried over Na2SO4, filtrated and concentrated in vacuo to give the title compound (4.4 g, 98%) as orange crystals which were pure enough for the next step without further purification.

Workup

  1. customevaporated
  2. washwashed with 2×80 ml water and 1×80 ml brine
  3. dry with materialThe organic phase were dried over Na2SO4
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0ec003c720a44df8207370b3ae72a49
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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