2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride → HCID 57505438, compound

HRID 1667828Notes

Reaction equation

HRID 1667828 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:10][N:11]1[C:15]([C:16](Cl)=[O:17])=[CH:14][C:13]([CH3:19])=[N:12]1>CN(C)C(=O)C>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=1[NH:1][C:16]([C:15]1[N:11]([CH3:10])[N:12]=[C:13]([CH3:19])[CH:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 50700783-Amino-4-chlorophenol

Product 1

HCID 57505438HCID 57505438, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Reference Example 23 and using 3-amino-4-chlorophenol (920 mg, 6.4 mmol), 1,3-dimethyl-1H-pyrazole-5-carbonylchloride (1170 mg, 7.4 mmol) and N,N-dimethylacetamide (13 mL) as starting materials, N-(2-chloro-5-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (1190 mg, 4.5 mmol) was obtained. Using lithium aluminum hydride (1060 mg, 22 mmol), N-(2-chloro-5-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (1190 mg, 4.5 mmol) and tetrahydrofuran (40 mL) as starting materials, the title compound (810 mg, 72%) was obtained as a brown solid.

Sources & evidence

ORD record
ord-7b5b18e148cc4e4abaa190899d3916a4
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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