Phosphorus oxychloride → HCID 86608762, compound

HRID 407335Notes

Reaction equation

HRID 407335 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:13]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)O)[C:11]#[N:12].O=P(Cl)(Cl)[Cl:22]>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:13]([Cl:22])[C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)[C:11]#[N:12]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 7034362-Benzothiazol-2-yl-3-furan-2-yl-3-hydroxyacrylonitrile

Product 1

HCID 86608762HCID 86608762, compoundYield 94%

Conditions

Temperature
50 °C

Procedure

2-Benzothiazol-2-yl-3-furan-2-yl-3-hydroxyacrylonitrile (474 mg, 1.77 mmol) was suspended in POCl3 (5 mL). The suspension was first stirred at 50° C. for 1 hr then refluxed for 30 min until the solid dissolved completely. The resulting brown solution was poured over crushed ice (200 mL). The resulting solids were isolated by filtration, washed with water until the pH of the wash water became neutral, and air-dried to yield 477 mg (94%) of 2-benzothiazol-2-yl-3-chloro-3-furan-2-ylacrylonitrile. MS (m/z, ES+): 287.0 (Cl35M+1, 100%), 289.0 (Cl37M+1, 45%).

Workup

  1. temperaturethen refluxed for 30 min until the solid
  2. dissolutiondissolved completely
  3. additionThe resulting brown solution was poured
  4. customThe resulting solids were isolated by filtration
  5. washwashed with water until the pH of the wash water
  6. customair-dried

Sources & evidence

ORD record
ord-e09b717d8ba141ee87ebad1389523835
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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