Ethyl chloroformate → HCID 14459503, compound

HRID 1031478Notes

Reaction equation

HRID 1031478 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)[CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CC(C)=O.O>[CH2:32]([O:31][C:29]([N:17]1[CH2:18][CH2:19][N:14]([C:13]2[CH:12]=[CH:11][C:10]([C:20]3[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=3)=[CH:9][C:8]=2[F:7])[CH2:15][CH2:16]1)=[O:30])[CH3:33]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 14459477HCID 14459477, compound

Product 1

HCID 14459503HCID 14459503, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.2 g (8.6 mmol) of potassium carbonate are added to a solution of 1.0 g (3.4 mmol) of 6-[3-fluoro-4-(piperazin-1-yl)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone in 10 ml of acetone and 10 ml of water. When the suspension has cooled down to 0° C., 0.42 ml (4.4 mmol) of ethyl chloroformate are added and stirring is continued for 30 minutes. The precipitated solid is suction filtered, washed with 10 ml of acetone-water mixture and recrystallized from 40 ml of acetonitrile. 0.73 g (60%) of a colourless solid, m.p. 193°-194° C., are obtained.

Workup

  1. filtrationfiltered
  2. washwashed with 10 ml of acetone-water mixture
  3. customrecrystallized from 40 ml of acetonitrile

Sources & evidence

ORD record
ord-3d30ec6d851542f38524681141402c46
Source dataset
uspto-grants-1990_09
Patent number
US04954501

Reaction notes

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