Benzenesulfonyl chloride → HCID 14476480, compound

HRID 1904952Notes

Reaction equation

HRID 1904952 reaction equation
[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][C:3]=2[O:2]1.O1CCCC1.C([Li])CCC.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.O.C(Cl)Cl>[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[S:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:31])=[O:30])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 2607975H-[1,3]dioxolo[4,5-f]indoleHCID 178418339Butyllithium

Product 1

HCID 14476480HCID 14476480, compoundYield 109.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of 5,6-methylenedioxyindole (11.5 gm, 71 mmol) in freshly distilled tetrahydrofuran (60 ml) under a nitrogen atomosphere at -70° C. was added dropwise 1.6M n-butyllithium (50 ml, 80 mmol) over a one-half hour period. Then benzenesulfonyl chloride (10.5 ml, 82 mmol) was added dropwise. The reaction mixture was gradually warmed to room temperature and poured into water/methylene chloride The methlene chloride layer was separated, dried (anhydrous Na2So4), filtered and evaporated to give 23.4 gm of crude product. This solid was triturated with diethyl ether and the purified product collected by filtration (18.0 gm), mp 142°-145° C.

Workup

  1. customwas separated
  2. customdried (anhydrous Na2So4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-fb55be749cbe42f0a7e8338bb746f4a6
Source dataset
uspto-grants-1989_06
Patent number
US04840963

Reaction notes

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