Ethyl chloroformate → HCID 86758307, compound

HRID 2227509Notes

Reaction equation

HRID 2227509 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:11])=[CH:4][CH:3]=1.[C:26](=O)([O-])[O-].[K+].[K+].[C:32](Cl)(=[O:36])[O:33][CH2:34][CH3:35]>CN(C)C=O>[C:20]1([C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:26][C:32]([O:33][CH2:34][CH3:35])=[O:36])=[CH:3][CH:4]=2)=[CH:9][C:10](=[O:11])[NH:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 70158445HCID 70158445, compound

Product 1

HCID 86758307HCID 86758307, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

95 mg of 3-(4-hydroxyphenyl)-3-phenyl-N-(3-pyridylmethyl)acrylamide was reacted with 2 ml of dimethylformamide, 48 mg of anhydrous potassium carbonate and 0.04 ml of ethyl chlorocarbonate for 4 hours under a stream of argon. The reaction mixture was extracted with ethyl acetate three times, washed twice with water and once with brine, and then dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was evaporated and purified via column chromatography on silica gel (chloroform:methanol=20:1) to give ethyl [4-[1-phenyl-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenoxy]acetate (140 mg, yield: 100%) as an oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate three times
  2. washwashed twice with water and once with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. custompurified via column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-e86b5ae156264f76927e32376ce8767c
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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