Ammonia → HCID 89815500, compound

HRID 1487140Notes

Reaction equation

HRID 1487140 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[C:7]([NH:9][C:10]1([C:13](O)=[O:14])[CH2:12][CH2:11]1)=[O:8])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.C[N:26](C=O)C.N>ClCCl>[C:13]([C:10]1([NH:9][C:7](=[O:8])[C:6]2[CH:16]=[CH:17][CH:18]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:12][CH2:11]1)(=[O:14])[NH2:26]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 65450578HCID 65450578, compound

Product 1

HCID 89815500HCID 89815500, compoundYield 369.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension of 1-(3-nitrobenzamido)cyclopropanecarboxylic acid (0.38 g, 1.519 mmol) in dichloromethane (5 ml), oxalyl chloride (0.199 ml, 2.278 mmol) was added followed by DMF (0.024 ml, 0.304 mmol). Reaction mixture was stirred at room temperature for 3 hr. After complete dissolution of the compound, cold aqueous ammonia (5 ml) was added under cooling. Allowed and stirred the content at room temperature for 1 hr. concentrated the reaction mixture to remove dichloromethane and the obtained slurry was filtered to obtain titled compound (0.28 g, 74%).

Workup

  1. additionwas added
  2. customReaction mixture
  3. additionwas added
  4. temperatureunder cooling
  5. stirringAllowed and stirred the content at room temperature for 1 hr
  6. concentrationconcentrated the reaction mixture
  7. customto remove dichloromethane
  8. filtrationthe obtained slurry was filtered

Sources & evidence

ORD record
ord-e3dd5a3aacfc423ab167836dc744458a
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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