Potassium Carbonate → HCID 86632616, compound

HRID 2076138Notes

Reaction equation

HRID 2076138 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.C([N:23]=[C:24]=[S:25])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:1][C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:24]([NH2:23])=[S:25])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 670963804-(2,4-Dimethyl-1,3-oxazol-5-yl)aniline

Product 1

HCID 86632616HCID 86632616, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,4-dimethyl-oxazol-5-yl)-phenylamine (470 mg, 2.5 mmol, CAS 100060-02-41) 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 an off-white solid (420 mg, 68%). MS ISP (m/e): 248.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.80 (s, 1H, NH), 7.55 (d, 2H), 7.50 (d, 2H), 2.41 (s, 3H), 2.29 (s, 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-e982a970cb044d66ac90a01089a05a07
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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