Pyridine → 2,7-Bis(acetylamino)dibenzodioxin

HRID 905535Notes

Reaction equation

HRID 905535 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:23]=[CH:22][C:12]2[O:13][C:14]3[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:15]=3[O:16][C:11]=2[CH:10]=1.N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31].C1C[O:40][CH2:39][CH2:38]1>>[C:30]([NH:21][C:19]1[CH:18]=[CH:17][C:15]2[O:16][C:11]3[CH:10]=[C:9]([NH:8][C:39](=[O:40])[CH3:38])[CH:23]=[CH:22][C:12]=3[O:13][C:14]=2[CH:20]=1)(=[O:32])[CH3:31]

Participants

6

Reactant 5

HCID 1049PyridineHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 353540HCID 353540, compound

Product 1

HCID 578925072,7-Bis(acetylamino)dibenzodioxinYield 82%

Procedure

To a mixture of 900 ml of toluene and 900 ml of THF were added 50.0 g (0.233 mole) of 2,7-diaminodibenzodioxin and 55.3 g (0.699 mole) of pyridine and to the resulting mixture was added 59.5 g (0.583 mole) of acetic anhydride in drops over a period of 10 minutes at room temperature with stirring. After the dropwise addition, the mixture was stirred overnight and a precipitate was recovered by filtration. The precipitate was reslurried with toluene (250 mix 2) and dried under reduced pressure to give 57.0 g (0.191 mole, 82.0% yield) of 2,7-bis(acetylamino)dibenzodioxin. The product showed a purity of 99.3 area % (HPLC, 254 nm).

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture was stirred overnight
  3. filtrationa precipitate was recovered by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f8b39272b061425faf50cd80b618c9b3
Source dataset
uspto-grants-2011_09
Patent number
US08012606B2

Reaction notes

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