Phosphorus oxychloride → HCID 86608760, compound

HRID 2261668Notes

Reaction equation

HRID 2261668 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](O)[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:11]#[N:12].O=P(Cl)(Cl)[Cl:26]>>[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:26])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:11]#[N:12]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136335804HCID 136335804, compound

Product 1

HCID 86608760HCID 86608760, compoundYield 95%

Conditions

Temperature
100 °C

Procedure

The above prepared 2-benzothiazol-2-yl-3-hydroxy-3-(4-nitrophenyl)-acrylonitrile (500 mg, 1.55 mmol) was suspended in POCl3 (12 mL). The suspension was heated at 100° C. for 4 hrs and was then poured into ice water (25 mL). The pH of the aqueous phase was adjusted to neutral. The solids were isolated by filtration and dried to yield 505 mg (95%) of 2-benzothiazol-2-yl-3-chloro-3-(4-nitrophenyl)-acrylonitrile. MS (m/z, ES+): 341.92 (Cl35M+1, 100%), 343.92 (Cl37M+1, 45%).

Workup

  1. customThe solids were isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-13c20e449a30459f9affd625df91e0b4
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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