Acetic Anhydride → HCID 18183126, compound

HRID 1359573Notes

Reaction equation

HRID 1359573 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>>[NH:1]([CH2:2][C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1)[C:26]([CH3:27])=[O:28]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18183123HCID 18183123, compound

Product 1

HCID 18183126HCID 18183126, compoundYield 70%

Procedure

0.72 g (2.13 mmol) of the aminomethyl compound from step B is dissolved in 6 ml of acetic anhydride at 25° C. and allowed to stand for 1 hour. The solution is diluted with ice water (30 ml) and stirred for 2 hours. The precipitated substance is filtered and, after drying by column chromatography, purified (silica gel, eluant ethyl acetate:benzene=4:1). After the fractions are concentrated by evaporation, 0.65 g of crystalline substance is obtained, which after washing with ethanol yields 0.56 g (70%) of pure title compound with a melting point of 205° C. (decomposition).

Workup

  1. filtrationThe precipitated substance is filtered
  2. customafter drying by column chromatography
  3. custompurified (silica gel, eluant ethyl acetate:benzene=4:1)
  4. concentrationAfter the fractions are concentrated by evaporation, 0.65 g of crystalline substance
  5. customis obtained
  6. washwhich after washing with ethanol

Sources & evidence

ORD record
ord-8eee00ecc3ae423dae9de89934382b56
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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