Phosphorus oxychloride → HCID 86608762, compound

HRID 57276Notes

Reaction equation

HRID 57276 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-341125418bb84f91b75cf9d3596ace81
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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