Hydrochloric Acid → HCID 21505986, compound

HRID 1287751Notes

Reaction equation

HRID 1287751 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:9]([S:13][C:14]1[C:22]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1[N+:27]([O-])=O)[CH2:10][CH2:11][CH3:12].Cl.[OH-].[Na+]>N.C(O)(C)C>[NH2:27][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([S:23](=[O:25])(=[O:26])[NH2:24])[C:14]=1[S:13][CH2:9][CH2:10][CH2:11][CH3:12])[C:18]([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 21506003HCID 21506003, compound

Product 1

HCID 21505986HCID 21505986, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of sodium dithionite (15.9 g) in aqueous ammonia (13 g NH3 in 150 ml water) 4-n-butylthio-3-nitro-5-sulphamyl-benzoic acid (8.35 g) was added in portions during 1 hour, while stirring. The reaction mixture was then heated on a steam bath for 30 minutes. Hydrochloric acid was added until the pH was 1, and heating was continued for 1 hour. After cooling, the pH was adjusted to 3 by the addition of 2N sodium hydroxide, and isopropanol (25 ml) was added. The precipitated 3-amino-4-n-butylthio-5-sulphamyl-benzoic acid was filtered off and recrystallized from aqueous ethanol. The melting point was 223°-224° C.

Workup

  1. temperatureThe reaction mixture was then heated on a steam bath for 30 minutes
  2. temperatureheating
  3. temperatureAfter cooling
  4. additionwas added
  5. filtrationThe precipitated 3-amino-4-n-butylthio-5-sulphamyl-benzoic acid was filtered off
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-740f3a42dd3b47e79c47067f98f7e422
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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