Benzoyl chloride → HCID 59369682, compound

HRID 45391Notes

Reaction equation

HRID 45391 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][CH3:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]([CH3:17])[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86642520HCID 86642520, compound

Product 1

HCID 59369682HCID 59369682, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude N-benzyl-4-methyl-2-(methylamino)thiazole-5-carboxamide (0.040 g, 0.15 mmol), 4-dimethylaminopyridine (catalytical amount) and triethylamine (64 μL, 0.45 mmol) in dichloromethane (5 mL) was added benzoyl chloride (19 μL, 0.17 mmol) at 0° C. and the reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction was quenched by the addition of saturated soldium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (30/70 to 50/50) to afford the title compound (0.040 g, 0.11 mmol); 1H NMR (CDCl3, 400 MHz) δ 7.47-7.35 (m, 5H), 7.30-7.17 (m, 5H), 6.05 (s, 1H), 4.51 (s, J=5.6 Hz, 2H), 3.55 (s, 3H), 2.60 (s, 3H); MS (ES+) m/z 366 (M+1).

Workup

  1. customThe reaction was quenched by the addition of saturated soldium bicarbonate solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with ethyl acetate/hexanes (30/70 to 50/50)

Sources & evidence

ORD record
ord-af29420bfb6a4876b0637362bd7930df
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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