Methanol → HCID 58214466, compound

HRID 389832Notes

Reaction equation

HRID 389832 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[N:15]=[C:14]([O:16][C:17]4[C:23]([CH3:24])=[CH:22][C:20]([NH2:21])=[C:19]([CH3:25])[CH:18]=4)[S:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CO.CO[CH:30](OC)[N:31]([CH2:33][CH3:34])[CH3:32]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[N:15]=[C:14]([O:16][C:17]4[C:23]([CH3:24])=[CH:22][C:20]([N:21]=[CH:30][N:31]([CH2:33][CH3:34])[CH3:32])=[C:19]([CH3:25])[CH:18]=4)[S:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23017846N-(dimethoxymethyl)-N-methylethanamineHCID 67080862HCID 67080862, compound

Product 1

HCID 58214466HCID 58214466, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.30 g (0.81 mmol) of 4-({3-[1-(4-chlorophenyl)cyclopropyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylaniline is dissolved in 3 ml of toluene and 0.75 ml of methanol and treated with 0.32 g (2.42 mmol) of N-ethyl-N-methylformamide dimethylacetal. The reaction mixture is refluxed for 18 h, subsequently cooled, freed from the solvent under vacuum and purified by column chromatography. 0.22 g of product is obtained (99.3% purity, 61.7% yield; log P (pH2.3)=2.28).

Workup

  1. temperatureThe reaction mixture is refluxed for 18 h
  2. temperaturesubsequently cooled
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-e0629ffd48704279b44f0b2498181358
Source dataset
uspto-grants-2013_02
Patent number
US08383139B2

Reaction notes

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