Formamide → HCID 9870170, compound
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([S:19][CH3:20])[C:3]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28].C(Cl)Cl.[CH:33]([NH2:35])=O>>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[N:35]=[CH:33][N:1]=[C:2]2[N:6]([C:7]3[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=3[Cl:18])[N:5]=[C:4]([S:19][CH3:20])[C:3]=12Participants
Conditions
- Temperature
- 150 °C
Procedure
A suspension of 669 mg (1.39 mmol) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2-chlorobenzoyl)-3-methylthiopyrazole in 5 mL of formamide was heated at 150° C. overnight. A pale yellow solid precipitated upon cooling of the reaction mixture. A total of 50 mL of water was added to the stirred suspension to complete the precipitation of the product which was filtered off and washed with water. An inseparable trace of starting material was observed in the product by thin layer chromatography (TLC) and so the above procedure was repeated on the mixture giving a brown solid containing no trace of starting material. Trituration of this solid with methylene chloride gave a pale yellow solution which was concentrated to give the desired product as a white crystalline solid, m.p. 156-158° C.
Workup
- customA pale yellow solid precipitated
- temperatureupon cooling of the reaction mixture
- additionA total of 50 mL of water was added to the stirred suspension
- customthe precipitation of the product which
- filtrationwas filtered off
- washwashed with water
- customgiving a brown solid
- additioncontaining no trace of starting material
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-0461f12e332045cda3ba08fa180424bd
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448265B1
Reaction notes
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