N,N-Dimethylaniline → 4-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine

HRID 2239833Notes

Reaction equation

HRID 2239833 reaction equation
CN(C)C1C=CC=CC=1.[CH3:10][S:11][C:12]1[NH:17][C:16](=O)[N:15]2[N:19]=[CH:20][CH:21]=[C:14]2[N:13]=1.CCOC1C=CC(N)=CC=1.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:16]1[N:15]2[N:19]=[CH:20][CH:21]=[C:14]2[N:13]=[C:12]([S:11][CH3:10])[N:17]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 90764-EthoxyanilineHCID 24813Phosphorus oxychlorideHCID 1354442592-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one

Product 1

HCID 129161154-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazineYield 81%

Procedure

N,N-Dimethylaniline (601 mg, 4.96 mmol) was added to a suspension of 2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one (1.88 g, 10.33 mmol) from 1c in POCl3 (29 mL). The reaction mixture was heated to reflux for 7 hours, and then cooled to room temperature, concentrated in vacuo, and diluted with cold water (110 mL). The resulting solid was collected by vacuum filtration, washed with cold water and hexane, and then air dried to give 1.68 g (81%) of 4-chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 hours
  3. concentrationconcentrated in vacuo
  4. additiondiluted with cold water (110 mL)
  5. filtrationThe resulting solid was collected by vacuum filtration
  6. washwashed with cold water and hexane
  7. customair dried

Sources & evidence

ORD record
ord-ce61337946b848c69d2c19809a46395b
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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