Phosphorus oxide (P4O10) → HCID 66747882, compound

HRID 2401998Notes

Reaction equation

HRID 2401998 reaction equation
[Br:1][C:2]1[S:3][C:4]([Br:19])=[CH:5][C:6]=1[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O>>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[C:7]([C:6]1[CH:5]=[C:4]([Br:19])[S:3][C:2]=1[Br:1])=[N:9][CH2:10][CH2:11]2

Participants

4

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 66748142HCID 66748142, compound

Product 1

HCID 66747882HCID 66747882, compound

Conditions

Temperature
150 °C

Procedure

To a mixture of 2,5-dibromo-N-[2-(3-chlorophenyl)ethyl]thiophene-3-carboxamide (5.15 g, 12.2 mmol) in xylenes (25.98 mL, 70.32 mmol) at 70° C. was added phosphorus pentoxide (13.0 g, 45.8 mmol) and then phosphoryl chloride (12.0 mL, 129 mmol). The mixture was heated at 150° C. for 60 h, then the mixture was cooled to rt. The solution was removed by decantation and washed with toluene twice. Water (20 mL) and 20% NaOH (20 mL) were added and the mixture was sonicated. The mixture was extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, and evaporated in vacuo to give a residue which was purified by chromatography to afford 6-chloro-1-(2,5-dibromo-3-thienyl)-3,4-dihydroisoquinoline as foam solid (2.8 g, 57%).

Workup

  1. temperaturethe mixture was cooled to rt
  2. customThe solution was removed by decantation
  3. washwashed with toluene twice
  4. additionWater (20 mL) and 20% NaOH (20 mL) were added
  5. customthe mixture was sonicated
  6. extractionThe mixture was extracted with EtOAc
  7. washThe organic layer was washed with water
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customto give a residue which
  11. customwas purified by chromatography

Sources & evidence

ORD record
ord-b17bcb88a44a4baf8d51a2c6feeb82dd
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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