Phosphorus oxychloride → HCID 118699730, compound

HRID 1773316Notes

Reaction equation

HRID 1773316 reaction equation
[S:1]1[CH:13]2[CH:4]([NH:5][C:6](=O)[C:7]3[CH2:8][NH:9][CH2:10][CH2:11][C:12]=32)[CH:3]=[CH:2]1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:7]2[CH2:8][NH:9][CH2:10][CH2:11][C:12]=2[C:13]2[S:1][CH:2]=[CH:3][C:4]=2[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 118699722HCID 118699722, compound

Product 1

HCID 118699730HCID 118699730, compoundYield 86%

Conditions

Temperature
82.5 °C

Procedure

A mixture of 3a,6,7,8,9,9b-hexahydrothieno[3,2-c]-2,7-naphthyridin-5(4H)-one (2.69 g, 13.04 mmol) in phosphorus oxychloride (70 ml) was heated at 80-85° C. with stirring for 24 hours and allowed to cool to room temperature. The excess solvent was removed in vacuo and the residue was carefully quenched with ice water. The aqueous mixture was treated with solid NaOH until product precipitation ceased (pH ˜5) and the off-white, amorphous solid was collected, washed with water, and dried to give the title compound (2.51 g, 86%).

Workup

  1. temperatureto cool to room temperature
  2. customThe excess solvent was removed in vacuo
  3. customthe residue was carefully quenched with ice water
  4. additionThe aqueous mixture was treated with solid NaOH until product precipitation
  5. customthe off-white, amorphous solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-10669537898c48a28b8809136fb8c7a1
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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