Ethyl chloroformate → HCID 20202887, compound

HRID 978441Notes

Reaction equation

HRID 978441 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:21](Cl)(=[O:25])[O:22][CH2:23][CH3:24]>CC1C=CC=CC=1C>[CH2:23]([O:22][C:21]([NH:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 20202886HCID 20202886, compound

Product 1

HCID 20202887HCID 20202887, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred mixture of 7 parts of ethyl 2-amino-4-(phenylmethoxy)benzoate and 45 parts of dimethylbenzene were added dropwise 3.25 parts of ethyl carbonochloridate. Upon completion, stirring was continued for 6 hours at reflux temperature. The reaction mixture was cooled and the solvent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 6.1 parts (71%) of ethyl 2-[(ethoxycarbonyl)-amino]-4-(phenylmethoxy)benzoate (15).

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was evaporated
  4. customThe residue was crystallized from 2,2'-oxybispropane
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-d0d9f360428f4b45b7dca319d1081029
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

Loading…