Ammonium Chloride → HCID 21264607, compound

HRID 567118Notes

Reaction equation

HRID 567118 reaction equation
C([Li])CCC.C(O[CH:9]([O:15]CC)[N:10]1[CH:14]=[CH:13][N:12]=[N:11]1)C.[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1C(N1CCCC1)=O.[Cl-].[NH4+]>O1CCCC1.CO>[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:9]([N:10]1[CH:14]=[CH:13][N:12]=[N:11]1)=[O:15]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 21264588HCID 21264588, compoundHCID 22280793N-diethoxymethyltriazoleHCID 178418339Butyllithium

Product 1

HCID 21264607HCID 21264607, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

At −20° C., 2.8 g (0.01 mol) of 23% pure n-butyllithium are added dropwise within 15 minutes to a solution of 1.7 g (0.01 mol) of N-diethoxymethyltriazole in 10 ml of tetrahydrofuran. Stirring is continued for 15 minutes at −20° C., and 1.48 g (0.005 mol) of N-[2-(2-methylphenoxymethyl)-benzoyl]-pyrrolidine dissolved in 10 ml of tetrahydrofuran are then added, and the mixture is stirred for a further 30 minutes at −20° C. 2 g of ammonium chloride and 10 ml of methanol are added and the mixture is heated under reflux for 15 minutes. The volatile components are removed under reduced pressure, the residue is admixed with water and extracted with ethyl acetate, and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The residue crystallizes when treated with a mixture of diethyl ether and petroleum ether in the ratio of 1:1. 0.5 g (17% of theory) of 3-[2-(2-methylphenoxymethyl)-benzoyl]-triazole of melting point 179° C. is obtained.

Workup

  1. additionare then added
  2. stirringthe mixture is stirred for a further 30 minutes at −20° C
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 15 minutes
  5. customThe volatile components are removed under reduced pressure
  6. extractionextracted with ethyl acetate
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue crystallizes when
  10. additiontreated with a mixture of diethyl ether and petroleum ether in the ratio of 1:1

Sources & evidence

ORD record
ord-7fad4519a66742d98c210b31681b77c6
Source dataset
uspto-grants-2001_01
Patent number
US06177459B1

Reaction notes

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