Hydrochloric Acid → HCID 178464661, compound

HRID 1396045Notes

Reaction equation

HRID 1396045 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:6][N:5]([C:7](=[N:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21]C(=O)C)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[NH:8][CH2:9][CH3:10])[N:4]=[CH:3]1.Cl.[OH-].[Na+]>CO>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([N:11]=[C:7]([N:5]2[CH2:6][C:2]([CH3:1])([CH3:25])[CH:3]=[N:4]2)[NH:8][CH2:9][CH3:10])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178464664HCID 178464664, compound

Product 1

HCID 178464661HCID 178464661, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

900 mg N-(4-{[(4,4-Dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-sulfamoyl}-phenyl) acetamide was dissolved in 5 mL MeOH, and 5 mL of concentrated HCl was added. The mixture was stirred overnight at room temperature. The mixture was basified with 2M NaOH, and extracted twice with DCM. The combined organic layers were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM/MeOH 99:1) to give 400 mg (50%) of 4-Amino-N-[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-benzenesulfonamide as an amorphous solid. 1H NMR (400 MHz, CDCl3) δ 1.15 (t, J=7 Hz, 3H), 1.20 (s, 6H), 3.42-3.51 (m, 2H), 3.74 (br.s., 2H), 4.00 (br.s., 2H), 6.62-6.68 (m, 2H), 6.71 (s, 1H), 6.90 (br.s., 1H), 7.67-7.73 (m, 2H).

Workup

  1. extractionextracted twice with DCM
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-7e776ce161f54d6dbfa8f3c6e4056b19
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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