Benzoic acid, 3-(aminosulfonyl)-, methyl ester → 3-(Hydroxymethyl)benzene-1-sulfonamide

HRID 734737

Reaktionsgleichung

Reaktionsgleichung von HRID 734737
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8](OC)=[O:9])(=[O:4])=[O:3].[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>C1COCC1.CCO>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 108836Benzoic acid, 3-(aminosulfonyl)-, methyl esterHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Produkt 1

HCID 231337993-(Hydroxymethyl)benzene-1-sulfonamideAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(aminosulfonyl)benzoate (520 mg, 2.4 mmol) in THF/EtOH (24 mL, 1:1), CaCl2 (533 mg, 4.8 mmol) and NaBH4 (363 mg, 9.6 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, and then quenched with water. 1 M aqueous citric acid (8 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (307 mg, 68%) as a white solid. MS (ES+) m/z 210 [M+Na]+.

Aufarbeitung

  1. customquenched with water
  2. addition1 M aqueous citric acid (8 mL) was added to the mixture
  3. extractionextracted with EtOAc (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6fcd892a34db43a98561236d2c9adf9e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

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