Phosgene → HCID 12848791, compound

HRID 1649098Notes

Reaction equation

[CH:1]1([CH:4]([OH:6])[CH3:5])[CH2:3][CH2:2]1.[C:7](Cl)(Cl)=[O:8].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]([CH3:25])[CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:14][CH:13]=1>CCOCC>[CH:1]1([CH:4]([O:6][C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]([CH3:25])[CH2:20][C:21](=[O:24])[NH:22][N:23]=3)=[CH:14][CH:13]=2)=[O:8])[CH3:5])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

4.3 g (49.9 millimoles) of 1-cyclopropylethanol are added dropwise to a stirred solution of 9.9 g (100 millimoles) of phosgene in 100 ml of absolute ether at 0° C. The reaction solution is then stirred for 1 hour at 0° C. followed by one hour at room temperature, and the excess phosgene is removed by means of a dry stream of nitrogen, after which the ether is removed under reduced pressure at room temperature. The 1-cyclopropylethyl chloroformate which is left (6.6 g) is reacted with 5.0 g (24.6 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone by the method described in Example 31. The reaction mixture is also worked up as described in Example 31. After recrystallizing the product first from dimethylformamide/water and then from ethanol/ether, 1.3 g (17% of theory) of 6-[p-(1-cyclopropylethoxycarbonylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone are obtained as colorless crystals of melting point 223°-224° C.

Workup

waitfollowed by one hour at room temperature
customthe excess phosgene is removed by means of a dry stream of nitrogen
customafter which the ether is removed under reduced pressure at room temperature
waitThe 1-cyclopropylethyl chloroformate which is left (6.6 g)
customAfter recrystallizing the product first from dimethylformamide/water

Sources & evidence

ORD record: ord-d4ed746f89824463a2de973f75cd179b
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415571

Reaction notes

Loading…