Sodium Carbonate → Sulfaethidole

HRID 1854274Notes

Reaction equation

HRID 1854274 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:5][N:4]=1)[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[S:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 745569N-[4-[[(5-Ethyl-1,3,4-thiadiazol-2-yl)amino]sulfonyl]phenyl]acetamide

Product 1

HCID 7181SulfaethidoleYield 69%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 110 (200 mg, 0.61 mmol) was suspended in 3 N HCl (3 mL) and the suspension heated to reflux for 30 min. Following neutralization with saturated aqueous Na2CO3 solution, the precipitated product was collected by filtration, washed with water (3×15 mL), and dried under vacuum. The residue was crystallized from MeOH to give the product (120 mg, 0.42 mmol, 69%) as a solid, mp 190-191° C.; 1H NMR (500 MHz, DMSO) δ 1.20 (3, t, J=7.5 Hz), 2.79 (2, q, J=7.5 Hz), 5.91 (2, S), 6.57 (2, d, J=8.5 Hz), 7.41 (2, d, J=8.5 Hz), 13.65 (1, s); 13C NMR (125 MHz, DMSO) δ 12.3, 23.6, 112.5, 127.1, 127.6, 152.5, 159.1, 166.8; MS (LCQ, ESI+) Calculated for C10H13N4O2S2 285.0. found 285.0 (M+H)+; HRMS (FAB+, m/z) Calculated for C10H13N4O2S2 285.0480. found 285.0478 (M+H)+.

Workup

  1. temperaturethe suspension heated
  2. temperatureto reflux for 30 min
  3. filtrationthe precipitated product was collected by filtration
  4. washwashed with water (3×15 mL)
  5. customdried under vacuum
  6. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-e0bdd68801f049b2a1437dbd2f27db9f
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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