Toluene → 2-(p-Chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one

HRID 973288Notes

Reaction equation

HRID 973288 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C@@H:8]2[CH2:11][CH2:10][C@H:9]2[C:12]([OH:14])=O)=O)=[CH:4][CH:3]=1.[NH:17]([CH2:19][CH:20]([OH:23])[CH2:21][CH3:22])[NH2:18].C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH:8]3[CH:9]([C:12](=[O:14])[N:17]([CH2:19][CH:20]([OH:23])[CH2:21][CH3:22])[N:18]=2)[CH2:10][CH2:11]3)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 41131272-HydroxybutylhydrazineHCID 18594281trans-2-p-Chlorobenzoylcyclobutane carboxylic acid

Product 1

HCID 227511492-(p-Chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a flask equipped with a stirrer, heating mantle and Dean - Stark water separator is charged 7.2 g (0.30 mole) of a mixture of cis-and trans-2-p-chlorobenzoylcyclobutane carboxylic acid, 3.5 g (0.033 mole) of 1-hydrazino-2-butanol and 100 ml. of toluene. The mixture is stirred and refluxed until the water layer in the Dean-Stark tube remains constant (ca. 5hr). The solvent is removed in vacuo on a rotary evaporator, and the residue is dissolved in hot diethyl ether and allowed to cool to room temperature. The resultant solid is filtered off and yields 2-(p-chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one(isomer B;m.p. 133°-135°). The filtrate is further concentrated to give Isomer A (m.p. 115.5°-119° C).

Workup

  1. customInto a flask equipped with a stirrer
  2. custom(ca. 5hr)
  3. customThe solvent is removed in vacuo on a rotary evaporator
  4. dissolutionthe residue is dissolved in hot diethyl ether
  5. filtrationThe resultant solid is filtered off

Sources & evidence

ORD record
ord-d8ebce3116c24fcca19487e67337ccae
Source dataset
uspto-grants-1977_10
Patent number
US04055644

Reaction notes

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