Water → HCID 67048344, compound

HRID 551179Notes

Reaction equation

HRID 551179 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[CH3:20])=[O:8].[K].CC(C)([O-])C.O>CN(C=O)C>[CH3:20][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:10]=1[N:9]1[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1=[O:8])[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 50987170Potassium tertbutoxideHCID 67049372HCID 67049372, compound

Product 1

HCID 67048344HCID 67048344, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

300 mg (1.00 mmol) methyl 4-(N-[4-chlorobutoxycarbonyl]-amino)-3-methylbenzoate are dissolved in 10 ml DMF combined with 168 mg (1.50 mmol) potassium-tert.-butoxide and stirred for 3 hours at 60° C. The reaction mixture is mixed with water and extracted 3 times with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down i. vac. Then the residue is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:2).

Workup

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

Sources & evidence

ORD record
ord-10bfa72e8ea24d3fb4957896e7d58399
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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