Triethylamine → HCID 57718403, compound

HRID 1985888Notes

Reaction equation

HRID 1985888 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].C(N(CC)CC)C.[CH3:23][N:24]([CH3:29])[S:25](Cl)(=[O:27])=[O:26]>O1CCCC1>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[N:15]([S:25]([N:24]([CH3:29])[CH3:23])(=[O:27])=[O:26])[CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 216625422-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole

Product 1

HCID 57718403HCID 57718403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound of Example 1 (100 mg, 0.5 mmol) and triethylamine (77 μl, 0.55 mmol) in anhydrous tetrahydrofuran (4 ml), was added dimethylsulphamoyl chloride (59 μl, 0.55 mmol). The reaction mixture was stirred at 60° C., under nitrogen, for 36 h and then concentrated in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate (10 ml) and the two layers were separated. The aqueous layer was extracted with ethyl acetate (10 ml) and the combined organic layers were dried (MgSO4) and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water (10 ml) and ethyl acetate (10 ml)
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (10 ml)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7f917d4a6dd4ad48965396c57afb308
Source dataset
uspto-grants-2009_06
Patent number
US07547718B2

Reaction notes

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