Sulfanilamide → HCID 9926933, compound

HRID 1454925Notes

Reaction equation

HRID 1454925 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.OC1C2N=NNC=2C=CC=1.C(N=C=NC(C)C)(C)C.[S:32]([NH2:42])(=[O:41])([C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1)=[O:33]>CN(C=O)C>[S:32]([C:34]1[CH:35]=[CH:36][C:37]([NH:40][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])=[CH:38][CH:39]=1)(=[O:33])(=[O:41])[NH2:42]

Participants

6

Reactant 4

HCID 5333SulfanilamideHCID 12734DiisopropylcarbodiimideHCID 78250Indazole-3-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 9926933HCID 9926933, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of indazole-3-carboxylic acid (324 mg, 2 mmol), hydroxybenzotriazole (297 mg, 2.2 mmol) and diisopropylcarbodiimide (344 μl, 2.2 mmol) in DMF (10 ml) is stirred for 30 min at room temperature. Sulphanilamide (380 mg, 2.2 mmol) is added. The reaction mixture is stirred overnight at room temperature and then filtered. The filtrate is evaporated and is then extracted with AcOEt/H2O. The organic phase is dried over MgSO4, filtered and evaporated under vacuum to give a yellow solid (640 mg). This compound is recrystallized successively from AcOEt/CH2Cl2 and AcOEt/MeOH.

Workup

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. extractionis then extracted with AcOEt/H2O
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-d26f5bdf75354b5cab357c53247a48ee
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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