Phosphorus oxychloride → HCID 86695165, compound

HRID 1504011Notes

Reaction equation

HRID 1504011 reaction equation
O[C:2]1[C:3]2[C:4]3[CH2:5][CH:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:2]1[C:3]2[C:4]3[CH2:5][CH:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470649HCID 178470649, compound

Product 1

HCID 86695165HCID 86695165, compoundYield 62.1%

Conditions

Temperature
90 °C

Procedure

A 250-mL round-bottom flask was charged with a solution of ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (10.10 g, 34.55 mmol, 1.00 equiv) in POCl3 (80 g, 521.75 mmol, 15.00 equiv) was stirred for 1 h at 90° C. in an oil bath under nitrogen. The resulting mixture was concentrated under vacuum. The residue was added dropwise to a cooled saturated aqueous sodium bicarbonate and extracted with 3×200 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to give the ethyl 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (6.67 g, 62%) as a yellow solid. MS: m/z 311, 313 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additionThe residue was added dropwise to a cooled saturated aqueous sodium bicarbonate
  3. extractionextracted with 3×200 mL of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3533f3ae42984345b3aaf266e87e0af4
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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