Ammonia → 2-(dimethoxymethyl)-5-methyl-4-(trifluoromethyl)-1H-imidazole

HRID 1424936

Reaction equation

HRID 1424936 reaction equation
[CH2:1]1[C:6](=O)[N:5](Cl)C(=O)[CH2:2]1.[F:9][C:10]([F:21])([F:20])C(C1(C)SCCCS1)=O.[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH:25]=O.[NH3:29]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[CH3:22][O:23][CH:24]([O:27][CH3:28])[C:25]1[NH:29][C:1]([CH3:2])=[C:6]([C:10]([F:21])([F:20])[F:9])[N:5]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 31398ChlorosuccinimideHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 866484802,2,2-Trifluoro-1-(2-methyl-1,3-dithian-2-yl)ethanone

Product 1

HCID 675492182-(dimethoxymethyl)-5-methyl-4-(trifluoromethyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent

Procedure

NCS (870 mg, 6.51 mmol) and silver nitrate (1.48 g, 8.71 mmol) were dissolved in acetonitrile (40 mL) and distilled water (10 mL). 2,2,2-Trifluoro-1-(2-methyl-1,3-dithian-2-yl)ethanone obtained in Example (36a) (500 mg, 2.17 mmol) was added, and the mixture was stirred for 40 minutes. Thereafter, dimethoxyacetaldehyde (5.76 M aqueous solution, 0.4 mL, 23.0 mmol) and 28% aqueous ammonia (2 mL) were added, and the mixture was stirred at room temperature for 18 hours. The reaction solution was filtered through celite and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

  1. distillationdistilled water (10 mL)
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. filtrationThe reaction solution was filtered through celite
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-671107ff5f2c4dceb2710698bd8a9fe9
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Linked notes

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