Methyl chloroacetate → HCID 10316709, compound

HRID 1742094Notes

Reaction equation

HRID 1742094 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:7](=[S:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Cl[CH2:22][C:23]([O:25][CH3:26])=[O:24]>COCCO>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:7]([S:10][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[N:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7295Methyl chloroacetateHCID 10356994HCID 10356994, compound

Product 1

HCID 10316709HCID 10316709, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A stirred solution of 2.00 g (6.84 mmole) of 5-n-butyl-2,4-dihydro-4-(4-nitrobenzyl)-3H-1,2,4-triazole-3-thione in 10 ml of 2-methoxyethanol was treated with 2.38 ml (1.77 g, 13.7 mmole) of N,N-disopropylethylamine followed by 1.20 ml (1.48 g, 13.7 mmole) of methyl chloroacetate. The solution was stirred at room temperature under N2 for 2 hours and then concentrated in vacuo at 45° C. The residual oil was partioned between 70 ml of ethyl acetate and 70 ml of H2O. The organic phase was washed with 70 ml of H2O and then with 50 ml of saturated NaCl solution. The ethyl acetate solution was dried (MgSO4), filtered, concentrated and dried in vacuo to yield 2.50 g (100%) of the titled compound as an oil, homogenous by TLC in 19:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 365 (M+1 )+.

Workup

  1. concentrationconcentrated in vacuo at 45° C
  2. washThe organic phase was washed with 70 ml of H2O
  3. dry with materialThe ethyl acetate solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f39af4302ee447419e50c695011125ad
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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