Water → HCID 67048388, compound

HRID 1629845Notes

Reaction equation

HRID 1629845 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])[C:5]([O:7][CH3:8])=[O:6].[K].[CH3:20][C:21](C)([O-])[CH3:22].C(Br)C=C.O>CN(C=O)C>[CH2:22]([N:12]([C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])[C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[CH3:1])[CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 50987170Potassium tertbutoxideHCID 67048349Methyl 3-methyl-4-[(1-oxo-4-penten-1-yl)amino]benzoate

Product 1

HCID 67048388HCID 67048388, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1.00 g (4.04 mmol) methyl 3-methyl-4-(pent-4-en-1-oyl-amino)-benzoate dissolved in 5 ml DMF are combined with 500 mg (4.37 mmol) potassium-tert.-butoxide and at 40° C. 350 μl (489 mg, 4.04 mmol) allylbromide are slowly added with stirring. Then the mixture is heated to 70° C. for 3 hours. Then the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate, evaporated down i. vac., the residue is applied to silica gel and purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 9:1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customevaporated down i
  4. custompurified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-fbfe152e3471467f8cae71985a0e58e7
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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