Acetic Anhydride → HCID 14099335, compound

HRID 1496829Notes

Reaction equation

HRID 1496829 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+:5].[OH:6][C:7]1[CH:20]=[C:19](O)[C:18]2[C:22]3=[C:23]4[C:11](=[C:12]([S:28]([O-:31])(=[O:30])=[O:29])[CH:13]=[C:14]([S:24]([O-:27])(=[O:26])=[O:25])[C:15]4=[CH:16][CH:17]=2)[CH:10]=[CH:9][C:8]=13.[Na+].[Na+].[C:34](OC(=O)C)(=[O:36])[CH3:35]>CN(C=O)C>[Na+:5].[C:1]([O:4][C:19]1[CH:20]=[C:7]([O:6][C:34](=[O:36])[CH3:35])[C:8]2[C:22]3=[C:23]4[C:15](=[C:14]([S:24]([O-:27])(=[O:25])=[O:26])[CH:13]=[C:12]([S:28]([O-:31])(=[O:29])=[O:30])[C:11]4=[CH:10][CH:9]=2)[CH:16]=[CH:17][C:18]=13)(=[O:3])[CH3:2].[Na+:5]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium Acetate2×HCID 16212389Disodium 6,8-dihydroxypyrene-1,3-disulfonate

Product 1

HCID 14099335HCID 14099335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound (2) was prepared by the protocol already published [D2], but modified here. The modification was that sodium acetate was used [D3]. A mixture of sodium 6,8-dihydroxypyrene-1,3-disulfonate (1) (4.452 g, 10.16 mmol), sodium acetate (83.0 mg, 1.016 mmol) and acetic anhydride (5.8 mL) in DMF (250 mL) was stirred intensively at room temperature for 48 h with the exclusion of light. The reaction mixture was filtered through a Celite-kieselguhr bed (h=0.5 cm), and DMF was stripped off on a rotary evaporator at 50° C. and 0.1 Torr. The residue was recrystallized from an ethanol/water mixture (70 ml:10 ml), washed with acetone and dried in vacuo to give a yield of 4.242 g (83%) as yellow powder (melting point 245-247° C. (decomposition)).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite-kieselguhr bed (h=0.5 cm), and DMF
  2. customwas stripped off on a rotary evaporator at 50° C.
  3. customThe residue was recrystallized from an ethanol/water mixture (70 ml:10 ml)
  4. washwashed with acetone
  5. customdried in vacuo

Sources & evidence

ORD record
ord-38c33e0b9ba5484ebea781ddd4d1f4fa
Source dataset
uspto-grants-2015_12
Patent number
US09199928B2

Reaction notes

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