Sulfuric Acid → HCID 58932548, compound

HRID 853869Notes

Reaction equation

HRID 853869 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:13]2[N:12]3[CH2:16][CH2:17][CH2:18][N:19]=[C:11]3[C:10]3(OCCC[O:20]3)[C:9]=2[CH:8]=1>>[Br:6][C:7]1[CH:15]=[CH:14][C:13]2[N:12]3[CH2:16][CH2:17][CH2:18][N:19]=[C:11]3[C:10](=[O:20])[C:9]=2[CH:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 58932538HCID 58932538, compound

Product 1

HCID 58932548HCID 58932548, compoundYield 101%

Procedure

To cold concentrated H2SO4 (4.2 mL) was added 8′-bromo-3′,4′-dihydrospiro[1,3-dioxane-2,10′(2′H)-pyrimido[1,2-a]indole] (0.400 g, 1.24 mmol) in four portions with cooling in an ice bath. The reaction was stirred at room temperature for one hr, poured onto ice and basified with the careful addition of NE4OH keeping the temp cold with an external ice bath. The reaction mixture was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound as a red solid (0.332 g, 100% ). Anal: Calc'd for C11H9BrN2O: C, 49.84; H, 3.42; N, 10.7. Found: C, 49.86; H, 3.37; N, 10.51. NMR (300 Mz, DMSO-d6): consistent. MS: (ESI+) m/z 265 [M+H], one bromine pattern observed. m.p. 166-168° C., black melt.

Workup

  1. temperaturewith cooling in an ice bath
  2. additionpoured onto ice
  3. additionbasified with the careful addition of NE4OH
  4. extractionThe reaction mixture was extracted with EtOAc (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8131a31433ea4ea0aee821a0058368ec
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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