Hydrochloric Acid → HCID 65751811, compound

HRID 1669359Notes

Reaction equation

HRID 1669359 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])(=[O:8])=[O:7].CO.Cl>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[CH2:12][OH:13])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 16768026509094-14-8

Product 1

HCID 65751811HCID 65751811, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4.0 g of 3-[(2-methoxyethyl)aminosulfonyl]benzoic acid in 200 ml of tetrahydrofuran was added dropwise a solution of 1.07 M borane-tetrahydrofuran complex in 43.5 ml of tetrahydrofuran under ice-cooling, and this was stirred for 30 minutes, and stirred at room temperature overnight. After 40 ml of methanol was added dropwise under ice-cooling, 100 ml of 2 N hydrochloric acid was added dropwise. After warmed to room temperature, the solvent was distilled off under reduced pressure, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3.0 g of oily 3-[(2-methoxyethyl)aminosulfonyl]benzyl alcohol.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature overnight
  3. temperaturecooling
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc2d83c6eeed407ead967657581dc4f6
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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