Hydrochloric Acid → HCID 10687015, compound

HRID 1451103Notes

Reaction equation

HRID 1451103 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[CH3:5][S:6]([NH:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:11]=1[CH:12]=[O:13])(=[O:8])=[O:7].[OH-].[K+].Cl>C(O)C.O>[OH:13][CH:12]([C:11]1[CH:14]=[C:15]([CH:16]=[CH:17][C:10]=1[NH:9][S:6]([CH3:5])(=[O:8])=[O:7])[C:18]([O:20][CH3:21])=[O:19])[CH2:4][N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14797Potassium HydroxideHCID 10825027HCID 10825027, compound

Product 1

HCID 10687015HCID 10687015, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Nitromethane (1.22 g, 0.02 mol) was added to an ice-cooled mixture of 2-(methanesulfonylamino)-5-(methoxycarbonyl)benzaldehyde (2.57 g, 0.01 mol) in ethanol and the mixture stirred for 10 min. To this mixture was added potassium hydroxide (1.23 g, 0.022 mol in 20 mL 90% ethanol) at 0° C. over a period of 20 min. The reaction mixture was further stirred at 0° C. for 0.5 h and then at room temperature for 4 h. The mixture was neutralized with 2N HCl and poured in water (100 mL). The mixture was extracted with chloroform, dried over sodium sulfate, filtered, and concentrated. The residue was passed through a column of silica gel eluting with chloroform:methanol (99:1 to 95:5). The desired pure fractions were combined, concentrated, recrystallized from ethyl acetate-hexane, and dried to give 0.8 g (25%) of methyl 3-[1-(R,S)-hydroxy-2-nitroethyl]-4-[(methylsulfonyl)amino]benzoate as off-white crystals, mp 148° C.

Workup

  1. temperaturecooled
  2. stirringThe reaction mixture was further stirred at 0° C. for 0.5 h
  3. waitat room temperature for 4 h
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationconcentrated
  9. customrecrystallized from ethyl acetate-hexane
  10. customdried

Sources & evidence

ORD record
ord-b88f99af2cde47f8ac665c2182545aef
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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