Hydrochloric Acid → HCID 57434740, compound

HRID 1787998Notes

Reaction equation

HRID 1787998 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[CH2:17][CH:16]=[CH:15][CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[In].Cl>O.O1CCCC1>[N:13]1([S:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[NH2:1])(=[O:12])=[O:11])[CH2:14][CH:15]=[CH:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5359967Indium2×HCID 57434737HCID 57434737, compound

Product 1

HCID 57434740HCID 57434740, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A 250 mL round bottom flask was equipped with a magnetic stirrer and charged with 1-(3-nitrobenzenesulfonyl)-2,5-dihydro-1H-pyrrole (Example 92, 9.32 mmol, followed by 3:1 water/tetrahydrofuran v/v (50 mL). Indium powder (37.3 mmol) was added, followed by concentrated HCl (55.9 mmol). The reaction gives a slight exotherm and the indium forms a solid metal chunk. After 24 hours, TLC (dichloromethane/silica) indicated the reaction was mostly complete. The indium was removed with a pair of tweesers to a separate waste stream and the reaction was neutralized with sodium bicarbonate. The aqueous mixture was extracted with ethyl acetate (150 mL), the organic layer dried (Na2SO4), filtered, and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and loaded onto a 600 mL sintered glass funnel charged with silica gel (400 g). The silica plug was eluted with 9:1 dichloromethane:ethyl acetate, collecting 100 mL fractions. Fractions containing the desired product were combined and the solvent was removed under diminished pressure to afford 3-(2,5-dihydropyrrole-1-sulfonyl)-aniline as a white, crystalline solid. 1.50 g, (72%). m.p.: 187-188° C. LC/MS: m/z 224.8 [C10H12N2O2S+H]+. 1H-NMR (CDCl3): δ 4.0 (b, 2H); 4.13 (s, 4H); 5.66 (s, 2H); 6.84-6.87 (d, 1H, J=7.9 Hz); 7.13-7.14 (s, 1H); 7.18-7.20 (d, 1H, J=7.7 Hz); 7.26-7.31 (t, 1H, J=7.8 Hz).

Workup

  1. customA 250 mL round bottom flask was equipped with a magnetic stirrer
  2. customThe reaction gives a slight exotherm
  3. customThe indium was removed with a pair of tweesers to a separate waste stream
  4. extractionThe aqueous mixture was extracted with ethyl acetate (150 mL)
  5. dry with materialthe organic layer dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  9. customloaded onto a 600 mL sintered glass funnel
  10. additioncharged with silica gel (400 g)
  11. washThe silica plug was eluted with 9:1 dichloromethane
  12. customethyl acetate, collecting 100 mL fractions
  13. additionFractions containing the desired product
  14. customthe solvent was removed under diminished pressure

Sources & evidence

ORD record
ord-5362103fe729464b9b00306f015dd742
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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