4-Nitrobenzenesulfonyl chloride → HCID 86755878, compound

HRID 365404Notes

Reaction equation

HRID 365404 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[C@H:26]1[C@H:21]([CH2:22][CH2:23][CH2:24][CH2:25]1)[N:20]=[C:19]2[C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[C@H:26]1[C@H:21]([CH2:22][CH2:23][CH2:24][CH2:25]1)[N:20]=[C:19]2[C:32]1[CH:33]=[CH:34][C:35]([N:38]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[S:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 86755876HCID 86755876, compound

Product 1

HCID 86755878HCID 86755878, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.45 g of 4-nitrobenzenesulfonyl chloride in 20 ml of methylene chloride are added dropwise to a solution of 2.0 g of (+/-)-cis-8,9-dimethoxy-6-(4-aminophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine in 50 ml of methylene chloride and 1.0 ml of triethylamine. The solution is stirred overnight at RT, extracted with water, and the organic phase is dried and concentrated. The residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate in the ratio 3:2. After concentration of the corresponding eluate fractions, the title compound of m.p. 234.5° C. is obtained.

Workup

  1. extractionextracted with water
  2. customthe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel using
  5. additiona mixture of petroleum ether/ethyl acetate in the ratio 3:2

Sources & evidence

ORD record
ord-94961f76b2e7479b855b1cb6d8259cc8
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

Loading…