tert-Butyldimethylsilyl chloride → HCID 136200580, compound

HRID 884444Notes

Reaction equation

HRID 884444 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.[Si](Cl)(C(C)(C)C)(C)C.CCN(C(C)C)C(C)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1.[F-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCCC1>[OH:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[S:43]

Participants

7

Reactant 5

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 87949Lawesson's reagentHCID 11062816N,N,N-Trimethyl(phenyl)methanaminium fluorideHCID 22142235HCID 22142235, compound

Product 1

HCID 136200580HCID 136200580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-hydroxy-4-morpholin-4-yl-benzamide (102 mg; 0.46 mmol) and t-butyldimethylsilyl chloride (73 mg; 0.48 mmol) in dry tetrahydrofuran (4 mL) was added Hunig's base (0.084 mL; 0.48 mmol) via syringe at room temperature under a nitrogen atmosphere. After stirring at room temperature for 4 hours, Lawesson's reagent was added (117 mg; 0.28 mmol) in one portion and the resulting solution was stirred for 16 hours. Benzyl trimethyl ammonium fluoride (1.84 mmol) then was added and stirring was continued for 2 hours longer. The reaction was concentrated at reduced pressure, and the residue re-dissolved in EtOAc (10 mL) and washed with water, 10% citric acid, 5% NaHCO3, and brine then dried (Na2SO4), filtered and concentrated in vacuo. The residue was then recrystallized from EtOAc/hexanes to provide the thioamide as a yellow solid (31 mg; 28%).

Workup

  1. stirringthe resulting solution was stirred for 16 hours
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. concentrationThe reaction was concentrated at reduced pressure
  5. dissolutionthe residue re-dissolved in EtOAc (10 mL)
  6. washwashed with water, 10% citric acid, 5% NaHCO3, and brine
  7. dry with materialthen dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was then recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-ee96988121d94d6383cc72f4e8c44e7f
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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