Sodium Carbonate → 2-Sulfanilamido-1,3,4-thiadiazole

HRID 1966879Notes

Reaction equation

HRID 1966879 reaction equation
[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([NH:16]C(=O)C)=[CH:12][CH:11]=1)(=[O:9])=[O:8].C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:2]2[S:1][CH:5]=[N:4][N:3]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 694845N-[4-[(1,3,4-Thiadiazol-2-ylamino)sulfonyl]phenyl]acetamide

Product 1

HCID 2347622-Sulfanilamido-1,3,4-thiadiazoleYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 102 (1.0 g, 3.6 mmol) was suspended in 3N HCl (10 mL) and heated to reflux for 30 min. The acidic mixture was neutralized with Na2CO3 solution. The precipitated product was collected by filtration, washed with water, and dried to give the product (450 mg, 1.8 mmol, 49%), mp 226° C. (lit1 mp 221-222° C.); 1H NMR (250 MHz, CDCl3) δ 5.95 (2, s), 6.57 (2, d, J=6.5 Hz), 7.41 (2, d, J=6.5 Hz), 8.68 (1, s), 14.03 (1, br s).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b6722aa0584d423791e09365a0dd512f
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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