Triethylamine → HCID 14627717, compound

HRID 581028Notes

Reaction equation

HRID 581028 reaction equation
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:15])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.C(N(CC)CC)C.Cl[C:26]([O:28][CH2:29][CH2:30][Cl:31])=[O:27]>ClCCl>[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH:15][C:26]([O:28][CH2:29][CH2:30][Cl:31])=[O:27])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123052-Chloroethyl chloroformateHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 14627717HCID 14627717, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg (1.70 mmol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole, 260 μl (1.87 mmol) of triethylamine and 40 mg of dichloromethane were stirred at room temperature, and 193 μl (1.87 mmol) of 2-chloroethyl chloroformate were added thereto and stirred for 21 hours. The reaction liquid was washed thrice with water and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from chloroform to obtain 507 mg of the intended compound as pale yellow crystals. (yield: 87%)

Workup

  1. customThe reaction liquid
  2. washwas washed thrice with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-c073bbf981534f10bd9ae172418e6e49
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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