Hydrochloric Acid → HCID 20229120, compound

HRID 1833302Notes

Reaction equation

HRID 1833302 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([OH:14])(=[O:13])=[O:12].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.Cl>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([S:11]([OH:14])(=[O:13])=[O:12])[CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 73102-Chloro-5-nitrobenzenesulfonic acidHCID 31268Pyrrolidine

Product 1

HCID 20229120HCID 20229120, compound

Procedure

72.4 Grams 2-chloro-5-nitrobenzenesulfonic acid was added in portions to 134 ml pyrrolidine, while keeping the temperature below 65° C. After the addition, the reaction was heated at reflux temperature with stirring for 7 hours and allowed to stand overnight at room temperature. The reaction was poured into 800 ml ice water and the solution made strongly acidic with concentrated HCl until light yellow crystals separated. The product was filtered, washed with a little dilute HCl and the moist cake was recrystallized from about 800 ml water to give 70.7 grams 5-nitro-2-pyrrolidinylbenzenesulfonic acid. m.p. = 178°-179° C. The nitro compound was reduced catalytically in ethanol with 5% palladium on carbon catalyst to give 5-amino-2-pyrrolidinyl-benzenesulfonic acid. m.p. = 255°-256° C.

Workup

  1. customthe temperature below 65° C
  2. additionAfter the addition
  3. temperaturethe reaction was heated
  4. temperatureat reflux temperature
  5. waitto stand overnight at room temperature
  6. customseparated
  7. filtrationThe product was filtered
  8. washwashed with a little dilute HCl
  9. customthe moist cake was recrystallized from about 800 ml water

Sources & evidence

ORD record
ord-4a613cfa5fe64b97abbf1772e6a3fb12
Source dataset
uspto-grants-1978_01
Patent number
US04066457

Reaction notes

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