Water → HCID 66681913, compound

HRID 530302Notes

Reaction equation

HRID 530302 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[N:2]1.[H-].[Na+].[CH3:15][C:16]1([CH3:24])[CH2:20][O:19][CH2:18][N:17]1[C:21](Cl)=[O:22].O>O1CCCC1.CN(C)C=O>[CH3:15][C:16]1([CH3:24])[CH2:20][O:19][CH2:18][N:17]1[C:21]([N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[N:2]1)=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 450813854,4-Dimethyl-1,3-oxazolidine-3-carbonyl chlorideHCID 178524184HCID 178524184, compound

Product 1

HCID 66681913HCID 66681913, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1H-benzo[d][1,2,3]triazole-5-carboxylic acid (3 g, 18.39 mmol) in a mixture of tetrahydrofuran (90 mL) and dimethylformamide (50 mL) was added dropwise to a stirred suspension of sodium hydride (1.839 g, 46 mmol) in tetrahydrofuran (30 mL) at 0° C. The suspension was allowed to stir at room temperature for 30 minutes before adding dropwise, at 0° C., a solution of 4,4-dimethyloxazolidine-3-carbonyl chloride (3.16 g, 19.31 mmol) in tetrahydrofuran (10 mL). The reaction mixture was allowed to stir at room temperature for 4 h. Water was added at 0° C. and the solvent was evaporated. A mixture of dichloromethane/isopropanol (7:3) was added and the organic layer was separated. The aqueous layer was re-extracted with dichloromethane and the combined organic layers were dried (MgSO4), filtered and evaporated. The orange residue was recrystallised from isopropanol to give a beige solid (840 mg) that was used in the next step without further purification.

Workup

  1. additionbefore adding dropwise, at 0° C.
  2. stirringto stir at room temperature for 4 h
  3. customthe solvent was evaporated
  4. additionA mixture of dichloromethane/isopropanol (7:3)
  5. additionwas added
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was re-extracted with dichloromethane
  8. dry with materialthe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe orange residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-feb5581f204e48d7975520fdeac93d85
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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