Ethyl isocyanatoacetate → HCID 68686509, compound

HRID 1991433Notes

Reaction equation

HRID 1991433 reaction equation
C[O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1.[N:12]([CH2:15][C:16](OCC)=[O:17])=[C:13]=[O:14]>C(Cl)Cl>[O:14]=[C:13]1[NH:12][CH2:15][C:16](=[O:17])[N:10]1[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:2])=[O:11]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 68686509HCID 68686509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13 mmol of methyl-3-aminobenzoate were dissolved in 20 ml DCM and 1.7 ml of ethyl isocyanatoacetate added. The reaction mixture was stirred at rt for 1 h. The solvent was evaporated and the resulting crude taken up in 50 ml acetone. 50 ml of aq. HCl (25%) were added and heated to reflux for 8 h. After evaporation of the organic layer the resulting solid was filtered off, washed with water and dried under vacuum. MS(ISO): 219.2 (M−H+)

Workup

  1. customThe solvent was evaporated
  2. addition50 ml of aq. HCl (25%) were added
  3. temperatureheated
  4. temperatureto reflux for 8 h
  5. customAfter evaporation of the organic layer the resulting solid
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-202b77821e664493bcc2985693f4488b
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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