Acetic Acid → US10023592, Example 152

HRID 575640Notes

Reaction equation

HRID 575640 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].[CH:8]1([CH2:11][O:12][C:13]2[C:14]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26](=[O:33])[N:25]([CH3:34])[CH:24]=3)=[N:15][C:16](S(C)(=O)=O)=[N:17][CH:18]=2)[CH2:10][CH2:9]1.C(O)(=O)C>CN(C=O)C>[CH:8]1([CH2:11][O:12][C:13]2[C:14]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26](=[O:33])[N:25]([CH3:34])[CH:24]=3)=[N:15][C:16]([NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[N:17][CH:18]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 118021982US10023592, Example 311

Product 1

HCID 118021881US10023592, Example 152Yield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.93 g, 23.37 mmol, 60% in mineral oil) was added to MeSO2NH2 (2.22 g, 23.37 mmol) in dry DMF (30 mL) at 0° C. over 15 min. The mixture was stirred at 0° C. for 1 h and the title compound of step 5 (3.00 g, 7.79 mmol) was added. The mixture was heated at 60° C. for 6 h. After cooling, ice water was added and the pH was adjusted to 5 with acetic acid. The suspended solids were collected and washed with MTBE (50 mL) to afford the title compound (3 g, yield: 96.7%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 9.80 (s, 1H), 8.53 (d, J=8.0 Hz, 1H), 8.42 (s, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.70 (m, 2H), 7.56 (t, J=7.6 Hz, 1H), 3.87 (d, J=7.2 Hz, 2H), 3.70 (s, 3H), 3.39 (s, 3H), 1.12 (m, 1H), 0.58 (m, 2H), 0.24 (m, 2H). LCMS: 401.1 (M+1)+

Workup

  1. temperatureThe mixture was heated at 60° C. for 6 h
  2. temperatureAfter cooling
  3. customThe suspended solids were collected
  4. washwashed with MTBE (50 mL)

Sources & evidence

ORD record
ord-883b629dd7524b44a5a0fe5b982edf1e
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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