Isopropyl chloroformate → HCID 12805011, compound

HRID 1649092Notes

Reaction equation

HRID 1649092 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl[C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18]>C1(C)C=CC=CC=1>[CH:20]([O:19][C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:18])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 161928Ici 109,081

Product 1

HCID 12805011HCID 12805011, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (29.5 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone, 4.0 g (32.6 millimoles) of isopropyl chloroformate and 100 ml of absolute toluene are refluxed for 16 hours. The product is filtered off at 10° C., washed first with toluene and then with water, and recrystallized twice from dimethylformamide/water. 4.3 g (50% of theory) of 4,5-dihydro-6-(p-isopropoxycarbonylaminophenyl)-5-methyl-3(2H)-pyridazinone are obtained as colorless crystals, of melting point 236°-237° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed first with toluene
  3. customwith water, and recrystallized twice from dimethylformamide/water

Sources & evidence

ORD record
ord-5cfd6db7939344a58b357ce1f92c9caf
Source dataset
uspto-grants-1983_11
Patent number
US04415571

Reaction notes

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