Methanol → 4-Hydroxy-3-(morpholine-4-sulfonyl)-benzoic Acid, Methyl Ester

HRID 277574Notes

Reaction equation

HRID 277574 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)(=[O:13])=[O:12].S(Cl)(Cl)=O.O.[CH3:25]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:25])=[O:7])=[CH:4][C:3]=1[S:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)(=[O:13])=[O:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl Chloride2×HCID 167726074-Hydroxy-3-(morpholine-4-sulfonyl)-benzoic acid

Product 1

HCID 537806074-Hydroxy-3-(morpholine-4-sulfonyl)-benzoic Acid, Methyl EsterYield 86%

Conditions

Temperature
0 °C

Procedure

The 4-hydroxy-3-(morpholine-4-sulfonyl)-benzoic acid (4.0 g, 14 mmol) was dissolved in methanol and cooled to 0° C. Thionyl chloride (5 mL) was added slowly to the stirring solution. The solution was allowed to stir 15 h under nitrogen at room temperature. Water (10 mL) was added slowly to neutralize the thionyl chloride, and the solvent was removed under reduced vacuum. The concentrated oil was partitioned between ethyl acetate and water, and the ethyl acetate phase was washed with saturated sodium bicarbonate solution twice. The ethyl acetate was washed with brine, and dried using magnesium sulfate. Solvent was removed under vacuum to yield the crude oil. The crude was purified using silica gel (eluent 40% ethyl acetate/hexane) to provide the title compound (3.73 g,86%) as a white solid: 1HNMR (DMSO-d6) δ11.8-11.9 (bs, 1H), 8.22 (d, J=2 Hz, 1H), 8.05 (dd, J=9 Hz, 2 Hz, 1H), 7.14 (d, 9 Hz, 1H), 3.84 (m, 3H), 3.62 (m, 4H), 3.11 (m, 4H); MS (EI): M+ 301; Anal.Calc. for C12H15NO6S: C, 47.83; H, 5.02; N, 4.65. Found: C, 47.58; H, 4.95; N, 4.65.

Workup

  1. customthe solvent was removed under reduced vacuum
  2. customThe concentrated oil was partitioned between ethyl acetate and water
  3. washthe ethyl acetate phase was washed with saturated sodium bicarbonate solution twice
  4. washThe ethyl acetate was washed with brine
  5. customdried
  6. customSolvent was removed under vacuum
  7. customto yield the crude oil
  8. customThe crude was purified

Sources & evidence

ORD record
ord-6a6fdff6a5c74c0084538614e4eed7e0
Source dataset
uspto-grants-2002_03
Patent number
US06355633B1

Reaction notes

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