Phosphorus oxychloride → HCID 88596891, compound

HRID 1503895Notes

Reaction equation

HRID 1503895 reaction equation
O[C:2]1[C:13]2[C:12]3[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9][C:8]=3[S:7][C:6]=2[N:5]=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[N:3]=[CH:4][N:5]=[C:6]2[C:13]=1[C:12]1[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9][C:8]=1[S:7]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470647HCID 178470647, compound

Product 1

HCID 88596891HCID 88596891, compoundYield 94%

Conditions

Temperature
110 °C

Procedure

Two 2000-mL 4-necked round-bottom flasks were charged with a solution of 15.3 (200 g, 718.58 mmol, 1.00 equiv) in POCl3 (2000 mL) at room temperature. The resulting solution was stirred for 2 h at 110° C. in an oil bath. The reaction mixture was cooled to room temperature and concentrated under vacuum. The reaction was then quenched by the addition of 1000 mL of ice-water. The resulting solution was extracted with 3×500 mL of ethyl acetate and the organic layers were combined. The combined organic layers were washed with 2×500 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 200 g (94%) of ethyl 2-[12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetate (15.4) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customThe reaction was then quenched by the addition of 1000 mL of ice-water
  4. extractionThe resulting solution was extracted with 3×500 mL of ethyl acetate
  5. washThe combined organic layers were washed with 2×500 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dbbed5ea72744fe48581e43c2194c904
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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