Diethylamine → HCID 13203396, compound

HRID 978031Notes

Reaction equation

HRID 978031 reaction equation
[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([N:21](CC)[CH2:22][CH3:23])[CH3:20].ClC(OCC(C)C)=O.C(NCC)C>CN(C)C=O>[CH2:19]([N:21]([CH2:22][CH3:23])[C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][N:10]=1)[CH3:20]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 142300655-(1-Phenyl-1,2,3,4-tetrazol-5-yl)valeric acid

Product 1

HCID 13203396HCID 13203396, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(1-Phenyl-1,2,3,4-tetrazol-5-yl)valeric acid (2.5 g) is dissolved in dimethylformamide (50 ml), and thereto is added triethylamine (1.1 g). To the mixture is added dropwise with stirring isobutyl chloroformate (1.5 g) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise with stirring diethylamine (0.9 g) at room temperature, and the mixture is stirred for 2 hours. After distilling off dimethylformamide under reduced pressure, acetone is added to the resulting residue, and the insoluble materials are filtered off. The mother liquor is concentrated and then purified by column chromatography (Kieselgel 60, made by Merck & Co.). By eluting with chloroform, there is obtained N,N-diethyl-5-(1-phenyl-1,2,3,4-tetrazol-5-yl)valeramide (1.2 g), colorless liquid, nD25 =1.5303.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 2 hours
  3. distillationAfter distilling off dimethylformamide under reduced pressure, acetone
  4. additionis added to the resulting residue
  5. filtrationthe insoluble materials are filtered off
  6. concentrationThe mother liquor is concentrated
  7. custompurified by column chromatography (Kieselgel 60, made by Merck & Co.)
  8. washBy eluting with chloroform

Sources & evidence

ORD record
ord-8b9bb20d5bfd481bbdb3e3a61760e092
Source dataset
uspto-grants-1987_05
Patent number
US04663323

Reaction notes

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