Aniline → HCID 178467950, compound

HRID 70052Notes

Reaction equation

HRID 70052 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][CH:11]([O:16][CH2:17][CH3:18])[CH2:12][N:13]=[C:14]=[NH:15])[CH3:9].CS(O)(=O)=O.[OH-].[Na+]>C(O)C>[CH2:17]([O:16][CH:11]([O:10][CH2:8][CH3:9])[CH2:12][NH:13][C:14]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[NH:15])[CH3:18]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 10749464N-(2,2-diethoxyethyl)carbodiimide

Product 1

HCID 178467950HCID 178467950, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aniline (1.66 g, 17.8 mmol) was dissolved in ethanol (25 mL), and N-(2,2-diethoxyethyl)carbodiimide (a), (2.82 g, 17.8 mmol), was added dropwise. Then methanesulfonic acid (1.71 g, 17.8 mmol) was added, and the mixture was warmed at reflux for 24 h. The reaction mixture was poured into NaOH (0.5 M) and extracted with CH2Cl2. Drying and concentration afforded a product that was subjected to flash chromatography to give the intermediate guanidine (b) (3.3 g, 73.8%). NMR (500 MHz, DMSO-d6) δ 7.27-6.90 (m, 5H), 4.55 (t, 1H), 3.76-3.70 (m, 2H), 3.60-3.54 (m, 2H), 3.35-3.34 (d, 2H), 1.22 (pent, 6H). MS: 249.8 (M−H)−; 252.1 (M+H)+.

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux for 24 h
  3. extractionextracted with CH2Cl2
  4. customDrying
  5. concentrationconcentration
  6. customafforded a product that

Sources & evidence

ORD record
ord-bd4e889ec77b4ab59013856aa493297f
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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