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Water → HCID 67048388, compound

HRID 2222498
Notes
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Reaction equation

HRID 2222498 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228Dimethylformamide
Solvent

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-95c35fa5dede4d53a15e3b060cbe0389
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07371743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes