Phosphorus oxychloride → HCID 86608760, compound

HRID 407330Notes

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

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 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

customThe solids were isolated by filtration
customdried

Sources & evidence

ORD record: ord-4b523e3a866c4459bf2b5ca1e5a54dfb
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754233B2

Reaction notes

Loading…