Methanol → HCID 59823517, compound

HRID 1426865Notes

Reaction equation

HRID 1426865 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1.Cl[C:14]1[S:15][C:16]([Cl:20])=[C:17]([Cl:19])[N:18]=1.CO>CN(C)C=O.C(OCC)(=O)C.O>[Cl:19][C:17]1[N:18]=[C:14]([O:11][C:7]2[C:6]([CH3:12])=[CH:5][C:4]([NH2:3])=[C:9]([CH3:10])[CH:8]=2)[S:15][C:16]=1[Cl:20]

Participants

8

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 765444-Amino-2,5-dimethylphenolHCID 3016564Trichlorothiazole

Product 1

HCID 59823517HCID 59823517, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1.3 g (33 mmol) sodium hydride (60% in oil) were added portionwise to a solution of 4.1 g (30.0 mmol) of 4-amino-2,5-dimethylphenol in 30 ml of dimethylformamide. After the gas evolution has stopped, 5.6 g (30 mmol) of 2,4,5-trichloro-1,3-thiazole were added and the reaction mixture was stirred for 1 h at 100° C. At ambient temperature 0.5 ml methanol, 10 ml of water and 100 ml of ethyl acetate were added successively. The organic layer was separated, the watery layer extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate. Concentration in vacuo and column chromatographie (petroleum ether/acetone 4/1) yielded 4.8 g (16.6 mmol, 55%) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline log P (pH=2.3)=3.4

Workup

  1. customThe organic layer was separated
  2. extractionthe watery layer extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationConcentration in vacuo and column chromatographie (petroleum ether/acetone 4/1)

Sources & evidence

ORD record
ord-cc9423bda7674ec0b551325e47a5ddde
Source dataset
uspto-grants-2015_01
Patent number
US08933107B2

Reaction notes

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