Dimethylformamide → HCID 54112244, compound

HRID 2217264Notes

Reaction equation

HRID 2217264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]12[C:14](=[O:15])[O:13][C:11](=[O:12])[CH:9]1[CH2:10]2.[Cl-].[Al+3].[Cl-].[Cl-].CN(C)C=O>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]([C@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7964ChlorobenzeneHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54112244HCID 54112244, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4.5 g (0.040 mol) of chlorobenzene and 5.0 g (0.0446 mol) of 1,2-cyclopropanedicarboxylic acid anhydride were successively added dropwise to a mixture of 60.0 g (0.45 mol) of anhydrous aluminium chloride and 9 mL (0.115 mol) of anhydrous dimethylformamide while maintaining a reaction temperature of 60° C. to 70° C. and the mixture was then kept at 70° C. for 1 hour. After cooling, the reaction mixture was stirred into a mixture of 500 g of crushed ice and 60 mL of concentrated hydrochloric acid, the precipitate was suction filtered, washed thoroughly with water and dried over Siccapent in a vacuum drying chamber at a temperature of 50° C. 7.8 g (87% of theoretical) of colorless crystals were obtained, m.p. 150° C.-153° C.

Workup

  1. temperaturewhile maintaining a reaction temperature of 60° C. to 70° C.
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. washwashed thoroughly with water
  5. customdried over Siccapent in a vacuum
  6. customdrying chamber at a temperature of 50° C
  7. custom7.8 g (87% of theoretical) of colorless crystals were obtained

Sources & evidence

ORD record
ord-7ab29fdcda124147be1fe219a48166a4
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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