Water → HCID 178512003, compound

HRID 925023Notes

Reaction equation

HRID 925023 reaction equation
[C:1]1([S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:20](#[N:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CCCCC>[C:1]1([S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH:10][C:20](=[NH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7505BenzonitrileHCID 3653932-(Phenylthio)anilineHCID 178418339Butyllithium

Product 1

HCID 178512003HCID 178512003, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Procedure as described for Amidine I using the following amounts and modifications: 10.06 g of 2-phenylthioaniline (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 5.20 mL of benzonitrile (51.0 mmol). After refluxing overnight, the solution was green-brown. Addition of water yielded a light brown solution with suspended solid. Solution was taken to dryness, resuspended in 75 mL of pentane, filtered, washed with 10 mL of pentane and dried in vacuo yielding 10.56 g (69%) of beige powder. NMR (400 MHz, C6D6): 7.76 (d, 2H), 7.42 (d, 2H), 7.31 (d, 1H), 7.1-6.8 (m, 8 H), 6.78(t, 1H), 4.08 (s, 2H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded a light brown solution
  3. filtrationfiltered
  4. washwashed with 10 mL of pentane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1fcdd63a48fb4a1c8b9c3823da358d30
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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