Water → HCID 90419071, compound

HRID 2202390Notes

Reaction equation

HRID 2202390 reaction equation
S(=[N:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[N:11]=[S:12]=O)=O.O.[Cl:15][S:16](O)(=[O:18])=[O:17]>>[F:10][C:6]1[C:5]2=[N:11][S:12][N:3]=[C:4]2[C:9]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 90418930HCID 90418930, compound

Product 1

HCID 90419071HCID 90419071, compound

Procedure

A solution of N,N′-disulfinyl-3-fluoro-1,2-diaminobenzene 39B (11.5 g, 52.75 mmol) in 80 mL of chlorosulfonic acid was heated at 110° C. for 8 hours. The mixture was cooled to r.t. and poured into water and extracted with EtOAc (50 mL) twice. The combined organic layer was washed with brine and dried over anhy. Na2SO4. The combined organic layer was concentrated in vacuo. Column chromatography (15% Petroleum/EtOAc) afforded 7.1 g of title compound. 1H NMR (CHLOROFORM-d) δ: 8.48 (dd, J=8.4 Hz, 4.4 Hz, 1H), 7.45 (t, J=8.4 Hz, 1H). LC-MS: m/z 253.2 (M+H)+.

Workup

  1. extractionextracted with EtOAc (50 mL) twice
  2. washThe combined organic layer was washed with brine
  3. customdried over anhy
  4. concentrationThe combined organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-63b908fccffe48e0881d8fde352d6139
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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