Phosgene → HCID 12805020, compound

HRID 1649093Notes

Reaction equation

HRID 1649093 reaction equation
OCC1CC1.C(Cl)(Cl)=O.Cl[C:11]([O:13][CH2:14][CH:15]1[CH2:17][CH2:16]1)=[O:12].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]([CH3:32])[CH2:27][C:28](=[O:31])[NH:29][N:30]=2)=[CH:21][CH:20]=1>CCOCC.C1(C)C=CC=CC=1>[CH:15]1([CH2:14][O:13][C:11]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]([CH3:32])[CH2:27][C:28](=[O:31])[NH:29][N:30]=3)=[CH:21][CH:20]=2)=[O:12])[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 75644CyclopropanemethanolHCID 161928Ici 109,081HCID 15917591Cyclopropylmethyl carbonochloridate

Product 1

HCID 12805020HCID 12805020, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3.2 g (44.4 millimoles) of (hydroxymethyl)cyclopropane, dissolved in 50 ml of absolute ether, are added dropwise to a stirred solution of 8.8 g (89.0 millimoles) of phosgene in 50 ml of absolute ether at 10°-15° C. The reaction solution is then stirred for 3 hours at room temperature. 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 cyclopropylmethyl chloroformate which remains is mixed with 6.0 g (29.5 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 100 ml of absolute toluene and the mixture is kept for 7 hours at 80° C. The product is filtered off at 10° C., washed first with toluene and then with water, and recrystallized twice from dimethylformamide/water. 3.0 g (34% of theory) of 6-(p-cyclopropylmethoxycarbonylaminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are obtained as colorless crystals of melting point 240°-241° C.

Workup

  1. customThe 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 7 hours at 80° C
  4. filtrationThe product is filtered off at 10° C.
  5. washwashed first with toluene
  6. customwith water, and recrystallized twice from dimethylformamide/water

Sources & evidence

ORD record
ord-9253a864865c4ca0827182453f9db111
Source dataset
uspto-grants-1983_11
Patent number
US04415571

Reaction notes

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