Phosphorus oxychloride → 2,3-Dioxoindoline-5-sulfonyl chloride

HRID 2191222Notes

Reaction equation

HRID 2191222 reaction equation
P(Cl)(Cl)([Cl:3])=O.[NH:6]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([OH:20])(=O)=[O:18])=[CH:14][CH:15]=2)[C:9](=[O:10])[C:7]1=[O:8].[Na]>C1S(=O)(=O)CCC1>[O:8]=[C:7]1[C:9](=[O:10])[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([S:17]([Cl:3])(=[O:20])=[O:18])[CH:12]=2)[NH:6]1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 817492,3-Dioxo-5-indolinesulfonic acidHCID 5360545Sodium

Product 1

HCID 159089472,3-Dioxoindoline-5-sulfonyl chlorideYield 83%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
60 °C

Procedure

(16) Phosphorus oxychloride (13.2 mL, 141.6 mmol) was added to a solution of 5-isatinsulfonic acid (5), sodium salt hydrate (8.0 g, 30.0 mmol) in tetramethylene sulfone (40 mL). The mixture was heated to 60° C. for 3 h, then cooled to 0° C. The reaction mixture was poured into 150 g of ice. The solid was filtered out and washed with cold water, then the solid was dissolved in ethyl acetate (100 mL), washed with water (50 mL×2) and saturated NaCl (50 mL), and dried over Na2SO4. The ethyl acetate was evaporated in reduced pressure to afford 6.12 g (83%) of 6 as a pale yellow solid, mp 188.2-190.1° C. 1H NMR (300 MHz, DMSO) δ 11.1 (s, 1H), 7.82 (dd, J=8.4 Hz, J=1.8 Hz, 1H), 7.60 (s, 1H), 6.89 (d, J=8.1 Hz, 1H).

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe solid was filtered out
  3. washwashed with cold water
  4. dissolutionthe solid was dissolved in ethyl acetate (100 mL)
  5. washwashed with water (50 mL×2) and saturated NaCl (50 mL)
  6. dry with materialdried over Na2SO4
  7. customThe ethyl acetate was evaporated in reduced pressure

Sources & evidence

ORD record
ord-a6965f5a4b1248bd8ddd9402ac4bb747
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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