Carbon Dioxide → HCID 135444586, compound

HRID 1742928Notes

Reaction equation

HRID 1742928 reaction equation
[C:1]([NH:7][C:8]1[C:9](=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)[C:10](O)=[O:11])(=O)[CH2:2][CH2:3][CH2:4][CH3:5].ClC(OCC)=O.C(=O)=O.[OH-].[NH4+:28]>CN(C)C=O.O.C(N(CC)CC)C>[CH2:2]([C:1]1[NH:28][C:10](=[O:11])[C:9]2[C:8](=[CH:16][CH:15]=[C:14]([I:17])[CH:13]=2)[N:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 5161967HCID 5161967, compound

Product 1

HCID 135444586HCID 135444586, compoundYield 56.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1500 g of N-valeryl-5-iodoanthranilic acid in 14.5 L of N,N-dimethylformamide is added under nitrogen, 660 mL of triethylamine. The resulting solution is cooled to 0° to 5° C. and 432 mL of ethyl chloroformate added over 10 minutes at a rate to maintain the temperature below 10° C. The reaction mixture is heated to 35° to 50° C. for 2 hours until the evolution of carbon dioxide ceases. Analysis of a small aliquot of the reaction mixture by GC/MS indicates 93.7% (area %) conversion. The reaction mixture is cooled to 10°-15° C. and 5.0 L of concentrated ammonium hydroxide added over 10 minutes. The resulting slurry is then heated at 60°-70° C. for 14 hours. To the reaction mixture is added 10 L of water and the resulting slurry cooled to ambient temperature and filtered. The recovered solid is washed with 3 L of a 1:1 water-N,N-dimethylformamide solution followed by two 3 L water washes. The solid is dried at 50° C. to give 803 g (56.7%) of the desired product. The purity is 100% as analyzed by GC/MS.

Workup

  1. additionis added under nitrogen
  2. temperatureThe resulting solution is cooled to 0° to 5° C.
  3. temperatureto maintain the temperature below 10° C
  4. temperatureThe reaction mixture is cooled to 10°-15° C.
  5. temperatureThe resulting slurry is then heated at 60°-70° C. for 14 hours
  6. filtrationfiltered
  7. washThe recovered solid is washed with 3 L of a 1:1 water-N,N-dimethylformamide solution
  8. customThe solid is dried at 50° C.

Sources & evidence

ORD record
ord-a4f85c6e50594d948474c9c2c8a30d46
Source dataset
uspto-grants-1994_08
Patent number
US05342944

Reaction notes

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