Sodium Methoxide → HCID 18009264, compound

HRID 2229917Notes

Reaction equation

HRID 2229917 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([CH3:33])=[C:8]([C:14]2([C:30]([NH2:32])=[O:31])[CH:18]([S:19](=[O:29])(=[O:28])[NH:20][C:21]3[O:25][N:24]=[C:23]([CH3:26])[C:22]=3[Cl:27])[CH:17]=[CH:16][S:15]2)[C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])(=O)C.C[O-].[Na+]>CO>[OH:4][CH2:5][C:6]1[C:7]([CH3:33])=[C:8]([C:14]2([C:30]([NH2:32])=[O:31])[CH:18]([S:19](=[O:28])(=[O:29])[NH:20][C:21]3[O:25][N:24]=[C:23]([CH3:26])[C:22]=3[Cl:27])[CH:17]=[CH:16][S:15]2)[C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18009284HCID 18009284, compound

Product 1

HCID 18009264HCID 18009264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-(4-chloro-3-methyl-5-isoxazolylsulfamoyl)-2-thiophenecarboxamide (Example 15) (250 mg, 0.49 mmol) in anh. MeOH (5 mL) was cooled to 0° C. and charged with 25% solution of sodium methoxide in MeOH (1.08 g, 5.0 mmol). Stirred for 30 min at 0° C. then the methanol was removed. Added 1N HCl (10 mL). The compound was taken into ethyl acetate. The extract was washed with water, brine, dried over MgSO4, concentrated. The residue was dissolved in ethyl acetate then the product was precipitated by addition of hexane. This gave 2-(3-hydroxymethyl-2,4,6-trimethylphenyl)-3-(4-chloro-3-methyl-5-isoxazolylsulfamoyl)-2-thiophenecarboxamide as a white powder (205 mg, 90%). 1H NMR (DMSO-d6)δ 1.99 (s, 3H); 2.11 (s, 3H); 2.22(s, 3H); 2.31 (s, 3H); 4.47 (s, 2H); 6.91 (s, 1H); 7.41 (d, 2H); 7.73 (d, 1H); 10.83 (s, 1H). IR (KBr) 3424, 2963, 1637, 1527, 1492, 1411, 1267, 1186, 1151, 1109 cm−1. Elemental analysis found: C, 48.50; H, 4.10; N, 8.63. C19H20ClN3O5S2 requires: C, 48.56; H, 4.29; N, 8.94.

Workup

  1. customthe methanol was removed
  2. additionAdded 1N HCl (10 mL)
  3. washThe extract was washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customthe product was precipitated by addition of hexane

Sources & evidence

ORD record
ord-498ec9b480254e4db0ffb25cde39cf11
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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