Ammonia → 1-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

HRID 1803168Notes

Reaction equation

HRID 1803168 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1)[NH2:5].[C:15](N1C=CC=CC1=O)([N:17]1C=CC=CC1=O)=[S:16].N>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]([NH2:17])=[S:16])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 575269743-Fluoro-4-(3-methyl-1H-1,2,4-triazol-1-YL)aniline

Product 1

HCID 866499181-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thioureaYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step Q (2): Dichloromethane (125 mL) was added to a flask charged with 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (5.00 g, 26.0 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (6.65 g, 28.6 mmol). The crude reaction was concentrated in vacuo. Methanolic ammonia (2.0 M, 150 mL, 300 mmol) was added at rt to the dark-red solid residue. A light brown precipitate resulted. After stirring for 30 min, the crude reaction mixture was chilled in a −20 C freezer for 1 h. The solid precipitate was collected using vacuum filtration. The solid was rinsed with cold methanol and dried under high vacuum to afford 1-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (5.48 g, 84% yield) as an off-white solid. LC-MS (M+H)+ 252.2. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.02 (br. s., 1 H), 8.80 (d, J=2.1 Hz, 1 H), 7.91 (dd, J=13.4, 2.1 Hz, 1 H), 7.66 (t, J=8.7 Hz, 1 H), 7.33 (dd, J=8.4, 2.0 Hz, 1 H), 2.36 (s, 3 H).

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated in vacuo
  3. customA light brown precipitate resulted
  4. customthe crude reaction mixture
  5. temperaturewas chilled in a −20 C freezer for 1 h
  6. customThe solid precipitate was collected
  7. filtrationvacuum filtration
  8. washThe solid was rinsed with cold methanol
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-9d25edb5da6f43a895b296290a6c97f2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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