Tetrahydrofuran → 2-Fluoro-N-thiazol-2-yl-4-thioureido-benzenesulfonamide

HRID 1644628Notes

Reaction equation

HRID 1644628 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)(=[O:14])=[O:13])=[C:8]([F:21])[CH:7]=1.C([N:25](CC)C(C)C)(C)C.O1CCCC1.[NH4+].[OH-]>>[F:21][C:8]1[CH:7]=[C:6]([NH:5][C:1]([NH2:25])=[S:2])[CH:11]=[CH:10][C:9]=1[S:12]([NH:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)(=[O:14])=[O:13]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10040ThiophosgeneHCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 575512254-Amino-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

Product 1

HCID 575512022-Fluoro-N-thiazol-2-yl-4-thioureido-benzenesulfonamideYield 36%

Procedure

Carbonothioic dichloride (25 uL, 0.00032 mol) was added to a mixture of the 4-amino-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (105 mg, 0.000271 mol) and N,N-diisopropylethylamine (0.14 mL, 0.00081 mol) in tetrahydrofuran (1.5 mL, 0.018 mol) at 0° C. and stirred for 40 min. Sat'd NH4OH solution was added to the reaction mixture and stirred for a few min. The reaction mixture was rotovaped to remove THF. The aq phase was acidified with 1.0 N HCl (pH 6), extracted with EtOAc (3×), dried, and was concentrated to give the crude product, which was purified via automated flash chromatography (silica gel, 25% EtOAc in hexanes to 100% EtOAc). 32 mg (36%) of the product was obtained as a yellow solid.

Workup

  1. stirringstirred for a few min
  2. customto remove THF
  3. extractionextracted with EtOAc (3×)
  4. customdried
  5. concentrationwas concentrated
  6. customto give the crude product, which
  7. customwas purified

Sources & evidence

ORD record
ord-6b4b96bbdd2a413ebaf1217ae8a5fd4c
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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