4-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxamide → HCID 53931156, compound

HRID 1459463Notes

Reaction equation

HRID 1459463 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([NH2:13])=O)=[CH:4][C:3]=1[Cl:14]>O(Cl)Cl>[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]#[N:13])=[CH:4][C:3]=1[Cl:14]

Participants

3

Reactant 1

HCID 540584804-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxamide

Product 1

HCID 53931156HCID 53931156, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 24646Chlorine monoxideSolvent

Conditions

Temperature
100 °C

Procedure

Intermediate 7 (0.12 mol) was added to phosporous oxychloride (120 ml) and the reaction mixture was stirred for 45 minutes at 100° C. The mixture was cooled and the solvent evaporated. The residue was added to ice and the mixture was extracted with CH2Cl2 and methanol. The organic layer was dried over MgSO4, filtered and the solvent evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 99/1). The pure fractions were collected and the solvent evaporated, yielding 14.5 g (63%) of 4-amino-5-chloro-2,3-dihydro-7-benzofuran-carbonitrile (intermediate 8).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent evaporated
  3. additionThe residue was added to ice
  4. extractionthe mixture was extracted with CH2Cl2 and methanol
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 99/1)
  9. customThe pure fractions were collected
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-b5d9c044938a4281b2398504091b5324
Source dataset
uspto-grants-1998_12
Patent number
US05854261

Reaction notes

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