Hydrochloric Acid → HCID 66924996, compound

HRID 554429Notes

Reaction equation

HRID 554429 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][C:15]([CH:24]=O)=[CH:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CO.[CH3:28][NH2:29].[BH4-].[Na+].[ClH:32].C(=O)([O-])O.[Na+]>CO>[ClH:32].[CH3:28][NH:29][CH2:24][C:15]1[CH:16]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]([S:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)(=[O:12])=[O:11])[CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86232870HCID 86232870, compound

Product 1

HCID 66924996HCID 66924996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(3-Nitrophenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (750 mg) was dissolved in methanol (50 mL), 40% methylamine methanol solution (1.64 g) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (240 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (100 mL) was added, and the mixture was stirred for 5 min. The reaction mixture was alkalized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure to give a free base of the title compound as a crude product. A part (50 mg) of the obtained crude free base was dissolved in methanol (10 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 43 mg, 5%).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was stirred for 5 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5aae84173b9a40b3addbdffe2fcaeb3b
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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