Phosgene → HCID 12805038, compound

HRID 1649097Notes

Reaction equation

HRID 1649097 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:9](Cl)(Cl)=[O:10].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:16][CH:15]=1>CCOCC>[CH:3]1([CH2:2][O:1][C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=3)=[CH:16][CH:15]=2)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 7507CyclohexanemethanolHCID 161928Ici 109,081

Product 1

HCID 12805038HCID 12805038, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.9 g (51.7 millimoles) of (hydroxymethyl)-cyclohexane are added dropwise to a stirred solution of 13.0 g (131.4 millimoles) of phosgene in 100 ml of absolute ether at 0°-10° C. The reaction solution is then stirred for 1 hour at 0°-10° C., and then for an 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 cyclohexylmethyl chloroformate which is left (8.5 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, then from ethyl acetate/petroleum ether and finally from acetone/water, 2.1 g (25% of theory) of 6-(p-cyclohexylmethoxycarbonylaminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are obtained as colorless crystals of melting point 223°-225° C.

Workup

  1. waitfor an hour at room temperature
  2. customthe excess phosgene is removed by means of a dry stream of nitrogen
  3. customafter which the ether is removed under reduced pressure at room temperature
  4. waitThe cyclohexylmethyl chloroformate which is left (8.5 g)
  5. customAfter recrystallizing the product first from dimethylformamide/water

Sources & evidence

ORD record
ord-d75b2917de6e428486cadcd51d38d190
Source dataset
uspto-grants-1983_11
Patent number
US04415571

Reaction notes

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