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Thionyl Chloride → 2-Chloro-5-benzoxazolecarbonitrile

HRID 1619271
Notes
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Reaction equation

HRID 1619271 reaction equation
S=[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[CH:10][C:4]=2[O:3]1.S(Cl)([Cl:15])=O>CN(C=O)C.C(Cl)Cl>[Cl:15][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 105114792-Thioxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrile

Product 1

HCID 106311802-Chloro-5-benzoxazolecarbonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
Temperature
67.5 °C

Procedure

To a mixture of 2-thioxo-2,3-dihydrobenzooxazole-5-carbonitrile (2.56 g, 14.5 mmol) and thionylchloride (14.1 mL) was added two drops of DMF. The mixture was heated at 65-70° C. for 1 h. Then the mixture was cooled to rt and diluted with CH2Cl2. The solvent and excess thionylchloride were removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: 20% EtOAc in Petroleum ether) to give 2-chlorobenzo-oxazole-5-carbonitrile 1.69 g (65%).

Workup

  1. temperatureThen the mixture was cooled to rt
  2. customThe solvent and excess thionylchloride were removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: 20% EtOAc in Petroleum ether)

Sources & evidence

ORD record
ord-2bf63788ebd64e0abb69a8badfc68823
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772285B2

Reaction notes

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