Carzenide → 4-(Hydroxymethyl)benzenesulfonamide

HRID 1162192Notes

Reaction equation

HRID 1162192 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[S:7]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)(=[O:10])(=[O:9])[NH2:8]>C1COCC1>[OH:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([S:7]([NH2:8])(=[O:9])=[O:10])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 8739CarzenideHCID 21226445Aluminium lithium hydride

Product 1

HCID 100811624-(Hydroxymethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

LiAlH4 (235 mg, 6.2 mmoles) was suspended in dry THF (10 mL) under nitrogen atmosphere. The suspension was cooled to 0° C. and 4-sulphamoyl-benzoic acid (500 mg, 2.48 mmoles, as a suspension in 10 mL of dry THF) was added. The resulting mixture was then refluxed for 18 hours. The reaction was quenched by addition of 3N HCl at 0° C. The quenched mixture was extracted with AcOEt, the organic layer was dried over Na2SO4 and evaporated to dryness. The crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 1/1) to yield the title compound in amount of 105 mg.

Workup

  1. temperatureThe resulting mixture was then refluxed for 18 hours
  2. customThe reaction was quenched by addition of 3N HCl at 0° C
  3. extractionThe quenched mixture was extracted with AcOEt
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 1/1)

Sources & evidence

ORD record
ord-0960529f39bd4ac8a00a4dc50c796b74
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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