Sodium Acetate → HCID 86602956, compound

HRID 734371Notes

Reaction equation

HRID 734371 reaction equation
C(COCC(CNC1C=C2C(=CC=1)N(CCCS([O-])(=O)=O)/C(=C\C=C\C=C1/S(=O)(=O)C3C=CC=CC=3C/1=O)/C2(C)C)=O)(O)=O.[Na+].[C:46]([CH2:49][O:50][CH2:51][C:52]([N:54]([CH3:87])[C:55]1[CH:86]=[CH:85][C:58]2[N:59]([CH2:78][CH2:79][CH2:80][S:81]([O-:84])(=[O:83])=[O:82])/[C:60](=[CH:62]/C=C/C=C3\S(=O)(=O)C4C=CC=CC=4C\3=O)/[S:61][C:57]=2[CH:56]=1)=[O:53])([OH:48])=[O:47].[Na+].CO/C=C/C=C1/S(=O)(=O)C2C=CC=CC=2C/1=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:46]([CH2:49][O:50][CH2:51][C:52]([N:54]([CH3:87])[C:55]1[CH:86]=[CH:85][C:58]2[N+:59]([CH2:78][CH2:79][CH2:80][S:81]([O-:84])(=[O:82])=[O:83])=[C:60]([CH3:62])[S:61][C:57]=2[CH:56]=1)=[O:53])([OH:48])=[O:47]

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 12067740HCID 12067740, compoundHCID 86602958HCID 86602958, compoundHCID 86602960HCID 86602960, compound

Product 1

HCID 86602956HCID 86602956, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Sodium 3-{(2Z)-5-{[(Carboxymethoxy)acetyl]methylamino}-2-[(2E,4Z)-4-(1,1-dioxido-3-oxo-1-benzothien-2(3H)-ylidene)but-2-enylidene]-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl}propane-1-sulfonate (24) and Sodium 3-{(2Z)-6-{[(Carboxymethoxy)acetyl]-methylamino}-2-[(2E,4Z)-4-(1,1-dioxido-3-oxo-1-benzothien-2(3H)-ylidene)but-2-enylidene]-1,3-benzothiazol-3(2H)-yl}propane-1-sulfonate (25). A mixture of the quaternary salt (22 or 23, 0.5 mmol) and enol ether 9 (0.625 g, 2.50 mmol) in 20 mL of a chloroformacetic acid mixture (1:1) was magnetically stirred at 60° C. under nitrogen. A solution of 0.200 g of sodium acetate in 5 mL of acetic acid was added by drops to the reaction mixture. The stirring was continued for an additional 24 h. After cooling the dye 25 crystallized from the reaction mixture and was separated by filtration and purified by recrystallization from acetic acid. The reaction mixture containing dye 24 was evaporated in a vacuum, and the pure dye was isolated by chromatography over silica gel, eluting with acetone-acetic acid (5:1), followed by recrystallization from acetic acid.

Workup

  1. temperatureAfter cooling the dye 25
  2. customcrystallized from the reaction mixture
  3. customwas separated by filtration
  4. custompurified by recrystallization from acetic acid
  5. additionThe reaction mixture containing dye 24
  6. customwas evaporated in a vacuum
  7. customthe pure dye was isolated by chromatography over silica gel
  8. washeluting with acetone-acetic acid (5:1)
  9. customfollowed by recrystallization from acetic acid

Sources & evidence

ORD record
ord-2b067257449d4720933b98646851e825
Source dataset
uspto-grants-2009_09
Patent number
US07592188B2

Reaction notes

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