Methanimidamide, N,N-diphenyl- → HCID 73681571, compound

HRID 851778Notes

Reaction equation

HRID 851778 reaction equation
[Br-:1].[OH:2][CH2:3][CH2:4][N+:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH3:15])=[CH:7][CH:6]=1.C1(N(C2C=CC=CC=2)C=N)C=CC=CC=1.[Br-].[OH:32][CH2:33][CH2:34][N+:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]([CH:45]=[CH:46]NC2C=CC=CC=2)=[CH:37][CH:36]=1>C(O)C>[Br-:1].[OH:2][CH2:3][CH2:4][N+:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[CH:46][CH:45]=[C:38]2[C:39]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:35]([CH2:34][CH2:33][OH:32])[CH:36]=[CH:37]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 78296Methanimidamide, N,N-diphenyl-HCID 120166911-(2-Hydroxyethyl)-4-methylquinolin-1-ium bromideHCID 70525732HCID 70525732, compound

Product 1

HCID 73681571HCID 73681571, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

On an oil bath, 2.7 g of 1-(2-hydroxyethyl)-4-methylquinolinium bromide and diphenylformamidine were heated for 5 minutes to melt them. Thereto was added 150 ml of ethanol, and the resulting mixture was boiled, upon which 1-(2-hydroxyethyl)-4-(2-anilinovinyl)-quinolinium bromide was crystallized. Then, 2.5 g of 1-hydroxyethyl-4-methylquinolinium bromide and 10 ml of triethylamine were added thereto and subjected to reaction under reflux for one hour. After completion of the reaction, the reaction product was cooled and the crude crystals thus obtained were recrystallized from methanol to obtain 2 g of the objective compound (melting point 262° C.) which was dark green. Its maximum absorption wavelength as measured in methanol was 707 nm.

Workup

  1. customwas crystallized
  2. additionThen, 2.5 g of 1-hydroxyethyl-4-methylquinolinium bromide and 10 ml of triethylamine were added
  3. customsubjected to reaction
  4. temperatureunder reflux for one hour
  5. customAfter completion of the reaction
  6. temperaturethe reaction product was cooled
  7. customthe crude crystals thus obtained
  8. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-abc1f3a6e629414085d9452d80fcc2e9
Source dataset
uspto-grants-1983_05
Patent number
US04386146

Reaction notes

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