4-Chloroisatoic anhydride → HCID 13952825, compound

HRID 580471Notes

Reaction equation

HRID 580471 reaction equation
[NH:1]1[CH:5]=[C:4](CCCCN)[N:3]=[CH:2]1.[Cl:11][C:12]1[CH:13]=[C:14]2[NH:20][C:19](=O)[O:18][C:16](=O)[C:15]2=[CH:22][CH:23]=1>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15]([C:16](=[O:18])[N:20]([CH2:14][CH2:13][CH2:12][CH2:23][N:3]3[CH:4]=[CH:5][N:1]=[CH:2]3)[CH:19]=[N:20]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 3291054-Chloroisatoic anhydrideHCID 178510959HCID 178510959, compound

Product 1

HCID 13952825HCID 13952825, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.39 g of imidazole-4-butanamine, 1.98 g of 4-chloroisatoic anhydride and 25 ml of ethanol was left at room temperature for 20 hours and concentrated. The residue and 5 ml of triethyl orthoformate were heated in an oil bath at 100°-125° C. for 3 hours and concentrated. The mixture was treated with ether to obtain the desired product, mp 123°-125° C.

Workup

  1. concentrationconcentrated
  2. temperatureThe residue and 5 ml of triethyl orthoformate were heated in an oil bath at 100°-125° C. for 3 hours
  3. concentrationconcentrated
  4. additionThe mixture was treated with ether

Sources & evidence

ORD record
ord-00a6a36566784e918a75db289e5621d2
Source dataset
uspto-grants-1988_06
Patent number
US04753944

Reaction notes

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