Hydrochloric Acid → N-(t-butoxy)-5-(4-chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamide

HRID 1392363Notes

Reaction equation

HRID 1392363 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:57]([O:61][NH2:62])([CH3:60])([CH3:59])[CH3:58].Cl>C(#N)C.C(OCC)(=O)C>[C:57]([O:61][NH:62][C:13]([C:11]1[S:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[N:10]=1)=[O:15])([CH3:60])([CH3:59])[CH3:58]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2777907O-tert-butylhydroxylamineHCID 10045599HCID 10045599, compound

Product 1

HCID 86595683N-(t-butoxy)-5-(4-chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamideYield 51%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Part B; 5-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid (1.00 gram, 2.6 mmol) is suspended in anhydrous acetonitrile (20 mL) under a nitrogen atmosphere at room temperature. Diisopropylethylamine (DIPEA) (1.36 mL, 7.8 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (1.08 gram, 2.85 mmol) and O-tert-butylhydroxylamine.HCl (0.35 gram, 25.1 mmol) are successively added and the resulting mixture is stirred overnight at room temperature. The resulting mixture is concentrated in vacuo and dichloromethane is added. The resulting solution is successively washed with water and brine, dried over MgSO4, filtered and evaporated in vacuo. Subsequent flash chromatography (ethyl acetate:petroleum ether (40-60)=1:3 (v/v)) gives N-(t-butoxy)-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxamide (0.60 gram, 51% yield) as a white foam. 1H-NMR (400 MHz, CDCl3): δ 9.20 (s, 1H), 7.47 (t, J=2 Hz, 1H), 7.25-7. (m, 4H), 7.14 (dt, J=8 Hz, J=2 Hz, 2H), 1.36 (s, 9H).

Workup

  1. concentrationThe resulting mixture is concentrated in vacuo and dichloromethane
  2. additionis added
  3. washThe resulting solution is successively washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad8f21a2cfca437da949bc55155f3dc5
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

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