Ammonium Chloride → N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-amino-dibenzo[b,d]furan-1-carboxamide

HRID 1788089Notes

Reaction equation

HRID 1788089 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:31])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:27][CH:28]([F:30])[F:29])=[CH:13][CH:12]=1)=[O:10].[Cl-].[NH4+]>[Zn].C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:31])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:27][CH:28]([F:29])[F:30])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 10050271N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide

Product 1

HCID 10320896N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-amino-dibenzo[b,d]furan-1-carboxamide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Third, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with zinc. In particular, to a 250 mL 2-necked round bottom flask was added N′-(3,5-dichloropyrid-4-yl)-4-difluoro methoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (1.00 g, 2.14 mmol), sat.aq. ammonium chloride (30.0 mL), ethanol (10.0 mL) and zinc (0.84 g, 12.82 mmol). The reaction mixture was heated to 95° C. over the weekend. The solvent was removed in vacuo, DMF (14 mL) was added to the residue and heated to 50-55° C. until dissolution. The hot solution was filtered, washed with DMF (4 mL) and poured onto water (100 mL). The precipitate was filtered, washed with water (20 mL) and dried in a vacuum oven to yield the amine as a pale yellow solid (0.73 g, 79.4%). Purity 86.31% by HPLC.

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo, DMF (14 mL)
  3. additionwas added to the residue
  4. temperatureheated to 50-55° C. until dissolution
  5. filtrationThe hot solution was filtered
  6. washwashed with DMF (4 mL)
  7. additionpoured onto water (100 mL)
  8. filtrationThe precipitate was filtered
  9. washwashed with water (20 mL)
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-824f639efe49499785302908ee443f3a
Source dataset
uspto-grants-2009_03
Patent number
US07511150B2

Reaction notes

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