Water → HCID 23354596, compound

HRID 235278Notes

Reaction equation

HRID 235278 reaction equation
C(N(CC)CC)C.[NH:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][N:10]=[N:9]1.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>ClCCl>[CH2:22]([O:21][C:19]([N:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][N:10]=[N:9]1)=[O:20])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178470518HCID 178470518, compound

Product 1

HCID 23354596HCID 23354596, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a mixture of 20 ml of dichloromethane and 3.4 g (33.6 mmol) of triethylamine was dissolved 1.50 g (10.6 mmol) of ethyl tetrazol-5-carboxylate, and 3.75 g (34.6 mmol) of ethyl chloroformate was added dropwise at 0° C. After stirring overnight at 0° C. to room temperature, water was added to the reaction mixture, followed by phase separation. Then, the dichloromethane layer was successively washed with 5% sodium dihydrogenphosphate solution, 5% sodium hydrogencarbonate solution and water, dried with magnesium sulfate, and concentrated, which afforded 1.42 g of ethyl N-ethoxycarbonyltetrazol-5-carboxylate. Yield, 63%.

Workup

  1. additionwas added dropwise at 0° C
  2. customfollowed by phase separation
  3. washThen, the dichloromethane layer was successively washed with 5% sodium dihydrogenphosphate solution, 5% sodium hydrogencarbonate solution and water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-70e2c9b92ad44d8f8bddf22d145e40f3
Source dataset
uspto-grants-1997_01
Patent number
US05597929

Reaction notes

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