1-Butanol → HCID 86736066, compound

HRID 1112126Notes

Reaction equation

HRID 1112126 reaction equation
C1(C2C=CC=CC=2)C=CC(OC[CH:9]([OH:12])[CH2:10][OH:11])=CC=1.ClC1C=C(Cl)C=CC=1C(=[O:34])C[N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.CC1C=CC(S(O)(=O)=[O:43])=CC=1.C(O)CCC.[OH2:51]>O(CC)CC.CC1C=CC=CC=1C>[C:9]([OH:12])(=[O:34])[C:10]([OH:11])=[O:51].[C:9]([OH:12])(=[O:43])[C:10]([OH:11])=[O:51].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

8

Reactant 5

HCID 2631-ButanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 322321-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-oneHCID 1027223-[([1,1'-Biphenyl]-4-yl)oxy]propane-1,2-diol

Product 1

HCID 86736066HCID 86736066, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 13.7 parts of 3-([1,1'-biphenyl]-4-yloxy)-1,2-propanediol, 12.8 parts of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone, 16 parts of 4-methylbenzenesulfonic acid, 40 parts of 1-butanol and 225 parts of dimethylbenzene is stirred and refluxed for 7 days with water-separator. The reaction mixture is cooled and diluted with 1,1'-oxybisethane. The organic phase is washed with a diluted sodium hydroxide solution and with water, dried, filtered and evaporated. The residue is converted into the ethanedioate salt in 4-methyl-2-pentanone and 2,2'-oxybispropane. The salt is filtered off and crystallized from 4-methyl-2-pentanone, yielding 12.8 parts (39%) of A + B-1-[4-(1,1'-biphenyl]-4-ylmethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole diethanedioate; mp. 116.8° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washThe organic phase is washed with a diluted sodium hydroxide solution and with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-1b5b64408a6b4d2290265b531da0a892
Source dataset
uspto-grants-1978_10
Patent number
US04120869

Reaction notes

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