Water → 2-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide

HRID 533662Notes

Reaction equation

HRID 533662 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[CH2:11]([S:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=O)[CH3:12].CCN=C=N[CH2:28][CH2:29][CH2:30]N(C)C.N1C=C[CH:37]=[CH:36][CH:35]=1.[OH2:40]>>[CH2:11]([S:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]1[CH:28]=[CH:29][CH:30]=[CH:37][C:36]=1[C:35]([NH:10][C:4]1[C:5]([NH:8][CH3:9])=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:40])[CH3:12]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 45079842N2,5-Dimethylpyridine-2,3-diamine

Product 1

HCID 899217132-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide

Conditions

Temperature
120 °C

Procedure

A mixture of 5,N2-dimethylpyridin-2,3-diamine (1.13 g), 2-ethylsulfanylbenzoic acid (1.79 g), WSC (1.38 g), and pyridine (20 ml) was stirred with heating under reflux at 120° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.58 g of 2-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide (Compound (1B)-514).

Workup

  1. temperaturewith heating
  2. temperatureInto the reaction mixture cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f387bddc6ba4136ae4cca89b9643380
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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