Ammonia → 1-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenyl)thiourea

HRID 1803180Notes

Reaction equation

HRID 1803180 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[F:15])[N:3]=1.[C:16](N1C=CC=CC1=O)([N:18]1C=CC=CC1=O)=[S:17].N>ClCCl>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:14]=[CH:13][C:11]([NH:12][C:16]([NH2:18])=[S:17])=[CH:10][C:9]=2[F:15])[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 61347462HCID 61347462, compound

Product 1

HCID 866499211-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenyl)thioureaYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step T (3): Dichloromethane (100 mL) was added to a flask charged with 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluoroaniline (1.67 g, 8.10 mmol and 1,1′-thiocarbonyldipyridin-2(1H)-one (1.88 g, 8.10 mmol). The resulting mixture was stirred for 24 h at rt and concentrated in vacuo. A solution of ammonia (2.0 M in methanol, 50 mL, 100 mmol) was added to the crude solid. The heterogeneous mixture was stirred at rt for 2 h, then evaporated to dryness under reduced pressure using a rotory evaporator. The solid residue was triturated with anhydrous ethanol and chilled to 0° C. for 1 h. The solid was collected by vacuum filtration and dried under high vacuum to afford 1-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenyl)thiourea (1.10 g, 4.06 mmol, 50% yield) as a white powdery solid. LC-MS (M+H)+ 266.3. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.06 (s, 1 H), 7.91 (d, J=12.5 Hz, 1 H), 7.50 (t, J=8.5 Hz, 1 H), 7.35 (d, J=8.9 Hz, 1 H), 2.26 (s, 6 H).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe heterogeneous mixture was stirred at rt for 2 h
  3. customevaporated to dryness under reduced pressure
  4. customa rotory evaporator
  5. customThe solid residue was triturated with anhydrous ethanol
  6. temperaturechilled to 0° C. for 1 h
  7. filtrationThe solid was collected by vacuum filtration
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-5805e56dab6c420d9bf667dd657fc021
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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