Potassium Carbonate → [4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-thiourea

HRID 2076141Notes

Reaction equation

HRID 2076141 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[S:4][N:3]=1.C([N:22]=[C:23]=[S:24])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:23]([NH2:22])=[S:24])=[CH:9][CH:8]=2)[S:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 670959474-(3-Methyl-1,2,4-thiadiazol-5-yl)aniline

Product 1

HCID 86632617[4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-thioureaYield 71.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-methyl-[1,2,4]thiadiazol-5-yl)-phenylamine (81 mg, 0.42 mmol) in tetrahydrofurane (6.4 mL) was added benzoyl isothiocyanate (76 mg, 0.44 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was suspended in methanol (10.6 mL). Potassium carbonate (175 mg, 1.27 mmol) dissolved in water (5.3 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 with water and with diethyl ether to yield the title compound as a yellow solid (75 mg, 71%). MS ISP (m/e): 251.0 (100) [(M+H)+], 501.1 (83) [(2M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.04 (br s, 1H), 7.94 (d, 2H), 7.72 (d, 2H), 2.63 (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 with water and with diethyl ether

Sources & evidence

ORD record
ord-b9af8a33bcc2443b99b6cf924f13611a
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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