Acetic Acid → HCID 68812137, compound

HRID 1821148Notes

Reaction equation

HRID 1821148 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[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][C:15]=3[O:16][C:11]=2[CH:10]=1.N1C=CC=CC=1.[C:30]([OH:33])(=O)[CH3:31].C1C[O:37][CH2:36][CH2:35]1>>[C:36]([NH:8][C:9]1[CH:23]=[CH:22][C:12]2[O:13][C:14]3[C:20]([NH:21][C:30](=[O:33])[CH3:31])=[CH:19][CH:18]=[CH:17][C:15]=3[O:16][C:11]=2[CH:10]=1)(=[O:37])[CH3:35]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 1049PyridineHCID 1140TolueneHCID 8028TetrahydrofuranHCID 68812412HCID 68812412, compound

Product 1

HCID 68812137HCID 68812137, compoundYield 82%

Procedure

To a mixture of 900 ml of toluene and 900 ml of THF were added 50.0 g (0.233 mole) of 2,6-diaminodibenzodioxin and 55.3 g (0.699 mole) of pyridine and 59.5 g (0.583 mole) of anhydrous acetic acid was added in drops to the mixture over a period of 10 minutes with stirring at room temperature. After the dropwise addition was over, the mixture was stirred overnight and a precipitate was recovered by filtration. The precipitate was submitted to reslurrying with toluene (250 ml×2) and then dried under reduced pressure to give 57.0 g (0.191 mole) of N,N′-diacetyl-2,6-diaminodibenzodioxin in an 82.0% yield. The product showed a purity of 99.3 area % (HPLC, 254 nm).

Workup

  1. additionwas added in drops to the mixture over a period of 10 minutes
  2. additionAfter the dropwise addition
  3. stirringwas stirred overnight
  4. filtrationa precipitate was recovered by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0b6a697894724a2299c4dede735f0755
Source dataset
uspto-grants-2009_10
Patent number
US07605277B2

Reaction notes

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