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Dimethylformamide → 2-(4,6-Dimethoxy-2-triazinylamino)-2-(9-fluorenyl)acetic acid

HRID 2305372
Notes
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Reaction equation

HRID 2305372 reaction equation
[NH2:1][CH:2]([CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:3]([OH:5])=[O:4].[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[NH:24][N:23](Cl)[N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O.C(OCC)(=O)C>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[NH:24][N:23]([NH:1][CH:2]([CH:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:3]([OH:5])=[O:4])[N:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2504002-amino-2-(9H-fluoren-9-yl)acetic acidHCID 221477162-Chloro-4,6-dimethoxy-triazine

Product 1

HCID 184328062-(4,6-Dimethoxy-2-triazinylamino)-2-(9-fluorenyl)acetic acidYield 29.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2.29 g (9.6 mmol) of 2-amino-2-(9-fluorenyl)acetic acid, 0.70 g (4.0 mmol) of 4,6-dimethoxy-2-chlorotriazine and 0.51 g (4.8 mmol) of sodium carbonate were introduced into a mixture of 16 ml of DMF and 16 ml of water and stirred at 80° C. for 13 hours. Then ethyl acetate and water were added and the phases were separated. The aqueous phase was acidified with 6 normal HCl and extracted three times with ethyl acetate. The organic phases were dried with MgSO4 and concentrated. The crude product was chromatographed on silica gel with ethyl acetate/n-heptane (1:1). 0.44 g (29.1%) of a white powder was obtained; RF=0.135, melting point 182-186° C.

Workup

  1. customthe phases were separated
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic phases were dried with MgSO4
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel with ethyl acetate/n-heptane (1:1)

Sources & evidence

ORD record
ord-1ec9a518fef24f69bb940d6171d03d1f
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06440975B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes