10578-09-3 → HCID 178463684, compound

HRID 1980155Notes

Reaction equation

HRID 1980155 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([OH:14])[N:8]2[C:12]([N:13]=1)=[N:11][CH:10]=[N:9]2)([OH:3])=O.[CH:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH2:16]>CN(C)C=O>[OH:14][C:7]1[N:8]2[C:12]([N:13]=[C:5]([CH2:4][C:1](=[O:3])[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]=[CH2:16])[CH:6]=1)=[N:11][CH:10]=[N:9]2

Participants

4

Reactant 2

HCID 1375105010578-09-3HCID 178525215HCID 178525215, compound

Product 1

HCID 178463684HCID 178463684, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

143 g of 6-carboxymethyl-4-hydroxy-1,3,3a,7-tetraazaindene prepared in Synthesis Example 1 and 98 g of vinylbenzylamine were dissolved in 1 l of dimethylformamide with stirring at room temperature. To the solution, 152 g of N,N-dicyclohexylcarbodiimide was added dropwise. After addition, the mixture was stirred at room temperature for 6 hours to separate white crystals (N,N-dicyclohexylurea). After the reaction, the separated crystals were filtered off and the filtrate was poured into 2 l of water to separate white crystals. The separated crystals were filtered out and recrystallized from acetonitrile to obtain 180 g of the desired 4-hydroxy-6-(N-vinylbenzylcarbamoylmethyl)-1,3,3a,7-tetraazaindene.

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred at room temperature for 6 hours
  3. customto separate white crystals (N,N-dicyclohexylurea)
  4. customAfter the reaction
  5. filtrationthe separated crystals were filtered off
  6. additionthe filtrate was poured into 2 l of water
  7. customto separate white crystals
  8. filtrationThe separated crystals were filtered out
  9. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-2c45347a5c1a46c4877f910b14d32d6f
Source dataset
uspto-grants-1984_11
Patent number
US04485169

Reaction notes

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