N-(dimethoxymethyl)-N-methylethanamine → N'-(2-Chloro-4-{[3-(1-chlorocyclopropyl)-1,2,4-thiadiazol-5-yl]oxy}-5-methylphenyl)-N-ethyl-N-methylimidoformamide

HRID 2194331Notes

Reaction equation

HRID 2194331 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[S:14][N:13]=[C:12]([C:15]3([Cl:18])[CH2:17][CH2:16]3)[N:11]=2)[C:6]([CH3:19])=[CH:5][C:3]=1[NH2:4].CO[CH:22](OC)[N:23]([CH2:25][CH3:26])[CH3:24]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[S:14][N:13]=[C:12]([C:15]3([Cl:18])[CH2:16][CH2:17]3)[N:11]=2)[C:6]([CH3:19])=[CH:5][C:3]=1[N:4]=[CH:22][N:23]([CH2:25][CH3:26])[CH3:24]

Participants

4

Reactant 2

HCID 23017846N-(dimethoxymethyl)-N-methylethanamineHCID 67079238HCID 67079238, compound

Product 1

HCID 44546591N'-(2-Chloro-4-{[3-(1-chlorocyclopropyl)-1,2,4-thiadiazol-5-yl]oxy}-5-methylphenyl)-N-ethyl-N-methylimidoformamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.63 g (1.86 mmol) of 2-chloro-4-{[3-(1-chlorocyclopropyl)-1,2,4-thiadiazol-5-yl]oxy}-5-methylaniline is dissolved in 5 ml of toluene and treated with 0.50 g (3.71 mmol) of N-ethyl-N-methylformamide dimethyl acetal. The reaction mixture is refluxed for 12 h, subsequently cooled, freed from solvent under vacuum and purified by column chromatography. 0.62 g of product is obtained (82.0% purity, 71.3% yield; log P (pH 2.3)=1.62).

Workup

  1. temperatureThe reaction mixture is refluxed for 12 h
  2. temperaturesubsequently cooled
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-9f184e422aec482db7c468337c3e2f4e
Source dataset
uspto-grants-2012_12
Patent number
US08334235B2

Reaction notes

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