Sodium Carbonate → Sulfamethizole

HRID 1854271Notes

Reaction equation

HRID 1854271 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17]C(=O)C)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[N:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([NH:7][C:5]2[S:6][C:2]([CH3:1])=[N:3][N:4]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 791566N-(4-(((5-Methyl-1,3,4-thiadiazol-2-yl)amino)sulphonyl)phenyl)acetamide

Product 1

HCID 5328SulfamethizoleYield 72.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 106 (250 mg, 0.8 mmol) was suspended in 3 N HCl (4 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 (3×20 mL), and dried under vacuum. The residue was crystallized from MeOH to give the product (155 mg, 0.58 mmol, 72%) as a solid, mp 207-208° C. (lit mp 208)1; 1H NMR (500 MHz, DMSO) δ 2.47 (3, s), 5.89 (2, s), 6.58 (2, d, J=8.5 Hz), 7.40 (2, d, J=8.5 Hz), 10.48 (1, s); 13C NMR (125 MHz, DMSO) δ 16.0, 112.5, 127.2, 127.6, 152.4, 153.6, 166.8.

Workup

  1. temperaturethe suspension heated
  2. temperatureto reflux for 30 min
  3. filtrationthe precipitated product was collected by filtration
  4. washwashed with water (3×20 mL)
  5. customdried under vacuum
  6. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-34bb1545e18d4b45864f64523c904264
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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