Chlorosuccinimide → HCID 86741865, compound

HRID 247154Notes

Reaction equation

HRID 247154 reaction equation
[CH:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][C:2]2=[C:10]1[CH2:17][CH2:16][CH:15]2[CH2:18][CH:11]1[CH2:12][CH2:13][CH2:14]2.[Cl:19]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:19][C:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][C:2]2=[C:10]1[CH2:17][CH2:16][CH:15]2[CH2:18][CH:11]1[CH2:12][CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 54344742HCID 54344742, compound2×

Product 1

HCID 86741865HCID 86741865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.82 mmol) of bicyclo[3,3,1]nonylidene-bicyclo[3,3,1]nonane (formula 17) in 20 cm3CH2Cl2, 115 mg (0.86 mmol) N-chlorosuccinimide was added. The reaction mixture was refluxed and stirred for 1 hour, and CH2Cl2 was added to dilute the reaction mixture. The organic layer was washed twice with water, dried with MgSO4 and evaporated. The yield of 4-eq.-chlorobicyclo[3,3,1]nonylidene-bicyclo[3,3,1]nonane was 190 mg. Purification was effected via chromatography (hexane, Al2O3) and sublimation (45° C./0.01 mm), melting point 50.53° C., 1H NMR (CDCl3) δ 4.4-3.9 (m, 1H); 3.1 (br s, 1H): 2.85 (br s, 3H); 2.5-1.2 (br, 22H); 13C NMR (CDCl3) δ 136.8 (s); 129.7 (s); 66.0 (d) and lines between 39.7 and 21.7; mass m/e 278:280 (3:1 ); exact mass: calculated 278.180; found 278.182.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. additionto dilute the reaction mixture
  3. washThe organic layer was washed twice with water
  4. dry with materialdried with MgSO4
  5. customevaporated
  6. customPurification
  7. customwas effected via chromatography (hexane, Al2O3) and sublimation (45° C./0.01 mm), melting point 50.53° C., 1H NMR (CDCl3) δ 4.4-3.9 (m, 1H); 3.1 (br s, 1H)

Sources & evidence

ORD record
ord-7d21081183114c89a24e4fc302c41d90
Source dataset
uspto-grants-1987_11
Patent number
US04705847

Reaction notes

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