Dimethylamine → HCID 58764261, compound

HRID 2387148Notes

Reaction equation

HRID 2387148 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[CH:11]=[O:12].[CH3:13][N:14](P(N(C)C)(N(C)C)=O)[CH3:15].CNC>O>[F:9][CH:8]([F:10])[C:4]1[C:3]([CH:11]=[O:12])=[C:2]([N:14]([CH3:15])[CH3:13])[N:6]([CH3:7])[N:5]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 12679HexamethylphosphoramideHCID 197546925-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 58764261HCID 58764261, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To mixture of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde (34 g, 0.17 mol) and HMPA (50 mL) was added a 40% aqueous solution of dimethylamine (66.3 mL). The reaction mixture was stirred for at 50° C. for 12 h, diluted with water (1 L), and the product was extracted with dichloromethane (2×100 mL). The combined organic layers were dried with sodium sulfate and evaporated. The liquid residue was purified chromatographically on silica gel using dichloromethane/ethyl acetate as eluent (1:3, Rf=0.25) to give 17.81 g (51.6%) of the title product. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, DMSO-d6): δ 2.93 (s, 6H), 3.72 (s, 6H), 7.07 (t, J=56 Hz, 1H), 9.94 (s, 1H). GC-MS calcd for C8H11F2N3O: 203.09, found (M+): 203 m/z.

Workup

  1. extractionthe product was extracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. customevaporated
  4. customThe liquid residue was purified chromatographically on silica gel

Sources & evidence

ORD record
ord-9f3e7752063c4d22a128dad8310a7ddf
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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