Ethyl 3-aminobenzoate → HCID 68687386, compound

HRID 1991432Notes

Reaction equation

HRID 1991432 reaction equation
C([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1)C.Cl[CH2:14][C:15]([N:17]=[C:18]=[O:19])=[O:16].C1CCN2C(=NCCC2)CC1>O1CCOCC1>[O:19]=[C:18]1[NH:17][C:15](=[O:16])[CH2:14][N:11]1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:3])=[O:12]

Participants

5

Reactant 3

HCID 11400Ethyl 3-aminobenzoateHCID 78209Chloroacetyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 68687386HCID 68687386, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12 mmol of ethyl-3-aminobenzoate were dissolved in 120 ml Dioxan. 1 eq of chloroacetyl isocyanate were added. The reaction mixture was stirred at rt for 1 h and then heated to 120° C. for an additional 2 h. The reaction was cooled to rt, 2 eq of DBU added and again stirred at rt overnight. The solvent was evaporated and the crude extracted from DCM. The crude material was dissolved in 20 ml MeOH and 4 ml of 4N NaOH were added. The reaction mixture was stirred at rt for 20 h. After evaporation of the organic layer the aqueous phase was acidified to pH=1 and the resulting white solid was filtered off and dried under vacuum. MS(ISO): 219.2 (M−H+)

Workup

  1. temperatureheated to 120° C. for an additional 2 h
  2. temperatureThe reaction was cooled to rt
  3. stirringagain stirred at rt overnight
  4. customThe solvent was evaporated
  5. extractionthe crude extracted from DCM
  6. dissolutionThe crude material was dissolved in 20 ml MeOH
  7. addition4 ml of 4N NaOH were added
  8. stirringThe reaction mixture was stirred at rt for 20 h
  9. customAfter evaporation of the organic layer the aqueous phase
  10. filtrationthe resulting white solid was filtered off
  11. customdried under vacuum

Sources & evidence

ORD record
ord-69da4efb645846c9aa2b49cdc53c8d8c
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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