Potassium Carbonate → HCID 86632615, compound

HRID 2076136Notes

Reaction equation

HRID 2076136 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:6][N:7]=1)[CH3:2].C([N:23]=[C:24]=[S:25])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH2:1]([C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:24]([NH2:23])=[S:25])=[CH:10][CH:9]=2)=[CH:6][N:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 12620624HCID 12620624, compound

Product 1

HCID 86632615HCID 86632615, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-ethyl-oxazol-5-yl)-phenylamine (470 mg, 2.5 mmol, CAS 73286-36-9) in tetrahydrofurane (20 mL) was added benzoyl isothiocyanate (449 mg, 2.8 mmol). The reaction was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was suspended in methanol (30 mL). Potassium carbonate (1036 mg, 7.5 mmol) dissolved in water (15 mL) was added drop wise to the suspension. The reaction was stirred at room temperature over night. The resulting solution was evaporated and the residue was stirred with water. The precipitate was filtered off, washed twice with water and twice with diethyl ether. The residue was dissolved in tetrahydrofurane and the solvent was removed under reduced pressure to yield the title compound as a light yellow solid (270 mg, 44%). MS ISP (m/e): 248.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ=9.80 (s, 1H, NH), 7.61 (d, 2H), 7.52 (d, 2H), 7.46 (s, 1H), 3.80 (q, 2H), 1.28 (t, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionwas added drop wise to the suspension
  3. stirringThe reaction was stirred at room temperature over night
  4. customThe resulting solution was evaporated
  5. stirringthe residue was stirred with water
  6. filtrationThe precipitate was filtered off
  7. washwashed twice with water and twice with diethyl ether
  8. dissolutionThe residue was dissolved in tetrahydrofurane
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-062aa9095c9048c9b7a67817ace1d0da
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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