Diisopropyl Ether → N-(1,5-dimethylpyrazol-3-yl)-2,6 dimethyl benzamide

HRID 128724

Reaction equation

HRID 128724 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH3:8])[N:3]=1.[CH3:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:11]=1[C:12](Cl)=[O:13].C([O-])(O)=O.[Na+].C(OC(C)C)(C)C>C(Cl)Cl.CCOC(C)=O>[CH3:8][N:4]1[C:5]([CH3:7])=[CH:6][C:2]([NH:1][C:12](=[O:13])[C:11]2[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:10]=2[CH3:9])=[N:3]1

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 890962,6-Dimethylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 70177471,5-dimethyl-1H-pyrazol-3-amine

Product 1

HCID 11776550N-(1,5-dimethylpyrazol-3-yl)-2,6 dimethyl benzamideYield 38.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0°-5° C.) solution of 3-amino-1,5-dimethyl pyrazole (95%, 32.7 g, 0.28M) in anhydrous CH2Cl2 (200 ml) was added a CH2Cl2 (100 ml) solution of the 2,6 dimethyl benzoyl chloride (23.6 g, 0.14M). The reaction mixture was allowed to room temperature for 18 hours and then CH2Cl2 was concentrated to give an oily mixture which was diluted in AcOEt. This suspension was then treated with saturated NaHCO3. After usual work-up, the crude material was cristallized with diisopropyloxide to give 13 g of the desired amide (38% : yield based on the 2,6-dimethyl benzoyl chloride).

Workup

  1. concentrationCH2Cl2 was concentrated
  2. customto give an oily mixture which

Sources & evidence

ORD record
ord-f98ffc91eb5e435fac5c17e51ecfdfc5
Source dataset
uspto-grants-1995_11
Patent number
US05464860

Linked notes

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