Phosgene → HCID 12805022, compound

HRID 1649094Notes

Reaction equation

HRID 1649094 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[C:6](Cl)(Cl)=[O:7].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]([CH3:24])[CH2:19][C:20](=[O:23])[NH:21][N:22]=2)=[CH:13][CH:12]=1.O1CCCC1>CCOCC>[CH:1]1([O:5][C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]([CH3:24])[CH2:19][C:20](=[O:23])[NH:21][N:22]=3)=[CH:13][CH:12]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 76218CyclobutanolHCID 161928Ici 109,081

Product 1

HCID 12805022HCID 12805022, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.0 g (69.3 millimoles) of cyclobutanol, dissolved in 80 ml of absolute ether, are added dropwise to a stirred solution of 11.5 g (116.3 millimoles) of phosgene in 100 ml of absolute ether at 10°-15° C. The reaction solution is then stirred for 3 hours at room temperature. Thereafter, the excess phosgene is removed by means of a dry stream of nitrogen, and the ether is then removed under reduced pressure at room temperature. The cyclobutyl chloroformate which remains in mixed with 6.0 g (29.5 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 180 ml of absolute tetrahydrofuran and the mixture is kept for 20 hours at room temperature and then for 4 hours at 40°-45° C. The product is filtered off at 10° C., washed first with tetrahydrofuran and then with water, and recrystallized from dimethylformamide/water. 2.8 g (31% of theory) of 6-(p-cyclobutoxycarbonylaminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are obtained as colorless crystals, of melting point 245°-246° C.

Workup

  1. customThereafter, the excess phosgene is removed by means of a dry stream of nitrogen
  2. customthe ether is then removed under reduced pressure at room temperature
  3. waitthe mixture is kept for 20 hours at room temperature
  4. waitfor 4 hours at 40°-45° C
  5. filtrationThe product is filtered off at 10° C.
  6. washwashed first with tetrahydrofuran
  7. customwith water, and recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-f99fb4d8726f433b8fb433225800592d
Source dataset
uspto-grants-1983_11
Patent number
US04415571

Reaction notes

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