Chlorosuccinimide → HCID 59032946, compound

HRID 1634715Notes

Reaction equation

HRID 1634715 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl:19]N1C(=O)CCC1=O>CN(C=O)C>[Cl:19][C:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:2]2[CH2:3][O:1]2)=[CH:7][CH:8]=1.[Cl:19][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:6]=1[O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Product 2

HCID 59032946HCID 59032946, compoundHCID 59032959HCID 59032959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.50 g, 2.09 mmol) and N-chlorosuccinimide (0.280 g, 2.09 mmol) in 5 mL dry DMF was stirred at ambient temperature for 48 hours. The reaction mixture was partitioned with EtOAc and H2O. The organic phase was washed with H2O and dried with Na2SO4. The solvent was removed (rotovap) and the residue purified by flash chromatography (methylene chloride-hexane-1:1) afforded 0.10 g of the title compound plus 0.50 g of 3-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole.

Workup

  1. customThe reaction mixture was partitioned with EtOAc and H2O
  2. washThe organic phase was washed with H2O
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed (rotovap)
  5. customthe residue purified by flash chromatography (methylene chloride-hexane-1:1)

Sources & evidence

ORD record
ord-420bbba7dd7e4683b5048af95a46fd4b
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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