Triethylamine → HCID 11419234, compound

HRID 748070Notes

Reaction equation

HRID 748070 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]([NH2:19])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:27][C:28]1[S:32][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:29]=1>C(Cl)Cl.CCOC(C)=O>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]([NH:19][S:33]([C:31]1[S:32][C:28]([Cl:27])=[CH:29][CH:30]=1)(=[O:35])=[O:34])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 68593891HCID 68593891, compound

Product 1

HCID 11419234HCID 11419234, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of [1-(1-benzyl-1H-imidazol-2-yl)-2-ethylbutyl]amine (448 mg, 1.74 mmol) in CH2Cl2 (15 mL) was added triethylamine (0.36 mL, 2.6 mmol) and 5-chlorothiophene-2-sulfonylchloride (453 mg, 2.09 mmol). The mixture was stirred for 3.5 h and then diluted with EtOAc, washed twice with 1N HCl, dried over MgSO4, filtered and concentrated in vacuo. The resulting oil was purified by column chromatography (SiO2, CHCl3, then 1% MeOH/CHCl3 to 2% MeOH/CHCl3) to yield a white solid in 59% yield.

Workup

  1. washwashed twice with 1N HCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was purified by column chromatography (SiO2, CHCl3
  6. custom1% MeOH/CHCl3 to 2% MeOH/CHCl3) to yield a white solid in 59% yield

Sources & evidence

ORD record
ord-d5227f5e731b4d78ab014ec72be50233
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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