1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 3356861, compound

HRID 2308573Notes

Reaction equation

HRID 2308573 reaction equation
[Cl:1][CH:2]([CH2:13]Cl)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:4].N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.O>[Cl:1][C:2](=[CH2:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20187066HCID 20187066, compound

Product 1

HCID 3356861HCID 3356861, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 17.0 grams (0.067 mole) of 2,3-dichloro-N-(4-chlorophenyl)propanamide (Step A product) in 300 ml of toluene was added dropwise 11.3 grams (0.074 mole) of 1,8-diazabicyclo[5.4.0]-undec-7-ene in 100 ml of toluene. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 60 hours. The reaction mixture was diluted with distilled water and transferred to a separatory funnel. The organic layer was separated and washed twice with water and twice with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual solid. The solid was recrystallized from methylcyclohexane using silica gel as a decolorant to give 7.4 grams of 2-chloro-N-(4-chlorophenyl)-2-propenamide; mp 105°-106.5°.

Workup

  1. additionUpon completion of addition
  2. customtransferred to a separatory funnel
  3. customThe organic layer was separated
  4. washwashed twice with water and twice with an aqueous solution saturated with sodium chloride
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residual solid
  8. customThe solid was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-d78261b5db40403182ceb5a845cd94f3
Source dataset
uspto-grants-1987_09
Patent number
USH0000327

Reaction notes

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