Cyclopropanecarbonyl chloride → HCID 19966735, compound

HRID 976230Notes

Reaction equation

HRID 976230 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[N:7]1([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:11]=[CH:10][CH:9]=[CH:8]1>ClCCCl>[CH:1]1([C:4]([C:8]2[N:7]([N:12]3[C:16](=[O:17])[C:15]4=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]4[C:13]3=[O:22])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

Product 1

HCID 19966735HCID 19966735, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Boron trifluoride-diethyl ether complex (10 g; 23.6×3 mM) was dissolved in 80 ml of 1,2-dichloroethane at 25° C., followed by adding dropwise cyclopropanecarbonyl chloride (7.4 g; 23.6×3 mM). After a suspension of N-(1H-pyrrol-1-yl)phthalimide (IX-1; 5 g; 23.6 mM) in 40 ml of 1,2-dichloroethane was added, the mixture was stirred at 25° C. for 18 hours. The reaction mixture was poured into ice-water and insoluble materials were removed by filtration. The 1,2-dichloroethane phase of the filtrate was separated and washed with a saturated saline solution, followed by drying with anhydrous sodium sulfate. After dried, it was concentrated and the resultant residue was purified with column chromatography on silica gel. White solid; m.p. 150°-2° C.; Yield 2.35 g (35.6%); HPLC purity 92% (254 nm) IR (KBr cm-1): 1803 1752 1647 1431 1398 1275 1236 1071 975 708 NMR(CDCl3, δ): 0.66~1.28(4H,m:cyclopropane ring CH2 --CH2) 2.16~2.5(1H,m:cyclopropane ring CH) 6.3(1H,dd,J=3,4 Hz:pyrrole ring C4) 6.9(1H,dd,J=2,3 Hz:pyrrole ring C3 or C5 ) 7.2(1H,dd,J=2,4 Hz:pyrrole ring C3 or C5 ) 7.5~8.0(4H,m:aromatic H)

Workup

  1. additionwas added
  2. customwere removed by filtration
  3. customThe 1,2-dichloroethane phase of the filtrate was separated
  4. washwashed with a saturated saline solution
  5. dry with materialby drying with anhydrous sodium sulfate
  6. customAfter dried
  7. concentrationit was concentrated
  8. customthe resultant residue was purified with column chromatography on silica gel

Sources & evidence

ORD record
ord-f665961395b74219a0ea62a737fdf7d0
Source dataset
uspto-grants-1997_03
Patent number
US05612287

Reaction notes

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