Dichloromethane → HCID 117860285, compound

HRID 1846426Notes

Reaction equation

HRID 1846426 reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.S(Cl)(Cl)=O.C(Cl)Cl.[N-:22]=[N+:23]=[N-:24].[Na+]>O.CN(C=O)C>[CH3:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([N:22]=[N+:23]=[N-:24])=[O:14])[CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 66978310HCID 66978310, compound

Product 1

HCID 117860285HCID 117860285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1.00 g (5.20 mmol) 4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carboxylic acid, 3.00 ml (41.1 mmol) thionyl chloride, 20 mL DCM and 1.0 mL DMF were combined and stirred for 4 h at 40° C. The reaction mixture was evaporated to dryness and co-evaporated with toluene. The residue was dissolved in acetone, combined with 340 mg (5.20 mmol) sodium azide and stirred for 1 h at RT. Then water was added, the precipitate formed was suction filtered and dried.

Workup

  1. customThe reaction mixture was evaporated to dryness and co-evaporated with toluene
  2. dissolutionThe residue was dissolved in acetone
  3. stirringstirred for 1 h at RT
  4. customthe precipitate formed
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-01b6a23cd4404a969a5eafe476090fe3
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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