Chlorosulfonic acid → HCID 58932540, compound

HRID 853854Notes

Reaction equation

HRID 853854 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11](=[O:20])[C:12]3[N:13]([CH2:16][CH2:17][CH2:18][N:19]=3)[C:14]=2[CH:15]=1>>[Cl:6][C:7]1[C:8]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:9][C:10]2[C:11](=[O:20])[C:12]3[N:13]([CH2:16][CH2:17][CH2:18][N:19]=3)[C:14]=2[CH:15]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 14181388HCID 14181388, compound

Product 1

HCID 58932540HCID 58932540, compoundYield 6%

Conditions

Temperature
71.5 °C

Procedure

Chlorosulfonic acid (6 mL, 90.3 mmol, 12.2 eq) was added slowly to solid 7-chloro-3,4-dihydropyrimido(1,2-a)indol-10-(2H)-one (1.64 g, 7.43 mmol) with cooling in an ice bath. The ice bath was removed and the reaction mixture was heated to 65-78° C. for 2 hours. After cooling to room temperature the reaction was added drop-wise via pipette onto ice keeping the temperature cold with an external ice bath. The reaction mixture was extracted with CHCl3 (3×) and CH2Cl2 (2×). The combined organic extracts were dried over MgSO4 and concentrated. The crude product was purified on Biotage KP silica gel eluting with EtOAc to give the title compound as a bright yellow solid (0.142 g, 6% yield). NMR (400 MHz, DMSO-d6): consistent.

Workup

  1. temperaturewith cooling in an ice bath
  2. customThe ice bath was removed
  3. temperatureAfter cooling to room temperature the reaction
  4. additionwas added drop-wise via pipette onto ice keeping the temperature cold with an external ice bath
  5. extractionThe reaction mixture was extracted with CHCl3 (3×) and CH2Cl2 (2×)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified on Biotage KP silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-f4733e36f9d2460d98cd7ee187cddcda
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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