Chlorosulfonic acid → HCID 135515526, compound

HRID 1066027Notes

Reaction equation

HRID 1066027 reaction equation
[O:1]1[C:5]2[C:6]([C:10]3[NH:11][C:12](=[O:23])[C:13]4[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=4[N:15]=3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:24][S:25](O)(=[O:27])=[O:26]>>[Cl:24][S:25]([C:8]1[CH:7]=[C:6]([C:10]2[NH:11][C:12](=[O:23])[C:13]3[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=3[N:15]=2)[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)(=[O:27])=[O:26]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 135418381HCID 135418381, compound

Product 1

HCID 135515526HCID 135515526, compound

Conditions

Temperature
0 °C

Procedure

Compound 5a (0.95 g, 0.003 mole) was added in portions to chlorosulfonic acid (2 ml) cooled to 0° C. (ice-bath) under stirring. The resulting yellow solution was then allowed to attain room temperature and was subsequently slowly heated to 65-70° C. (oil bath) for 1 h. The reaction mixture was then slowly poured onto crushed ice (25 g), whereby a white solid precipitated immediately. The white solid was filtered, dried and recrystallized from THF/petroleum ether (b.p. 40-60° C.), thereby yielding 6a.

Workup

  1. customto attain room temperature
  2. temperaturewas subsequently slowly heated to 65-70° C. (oil bath) for 1 h
  3. additionThe reaction mixture was then slowly poured
  4. customprecipitated immediately
  5. filtrationThe white solid was filtered
  6. customdried
  7. customrecrystallized from THF/petroleum ether (b.p. 40-60° C.)

Sources & evidence

ORD record
ord-2f5ae3b1142248a08554ac398c8c2af2
Source dataset
uspto-grants-2001_06
Patent number
US06242444B1

Reaction notes

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