Triethylamine → HCID 68515438, compound

HRID 1948300Notes

Reaction equation

HRID 1948300 reaction equation
C(N(CC)CC)C.[C:8]([NH2:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:10])[CH3:9].[CH3:18][S:19][C:20]1[S:21][CH:22]=[C:23]([C:25](Cl)=[O:26])[N:24]=1>C1COCC1>[CH3:9][C:8]([NH:17][C:25]([C:23]1[N:24]=[C:20]([S:19][CH3:18])[S:21][CH:22]=1)=[O:26])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 86643338HCID 86643338, compound2×

Product 1

HCID 68515438HCID 68515438, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (2.24 ml) was added to a solution of cumylamine (3.2 ml) in anhydrous THF (30 ml). After stirring for 15 min, a solution of 2-(methylthio)-4 -thiazolecarbonyl chloride (Intermediate 12; 3.1 g) in anhydrous THF was added and the reaction mixture was concentrated in vacuo after 15 min. The residue was partitioned with EtOAc and water, dried with MgSO4, and concentrated to an orange oil. Flash purification on silica gel with isocratic elution of DCM yielded the product as a yellow oil (3.7 g). MS (ES) MH+: 293 for C14H16N2OS2; NMR: 1.68 (s, 6H), 2.76 (s, 3H), 7.20 (d, J=7.16 Hz, 1H), 7.29 (t, J=7.54 Hz, 2H), 7.36-7.41 (m, 2H), 8.04 (s, 1H), 8.08 (s, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo after 15 min
  2. customThe residue was partitioned with EtOAc and water
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated to an orange oil
  5. customFlash purification on silica gel
  6. washwith isocratic elution of DCM

Sources & evidence

ORD record
ord-57edfa0147014fdbb1be3270d0e7d3f9
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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