Carbofuran → Glycine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(2-ethoxy-2-oxoethyl)-, ethyl ester

HRID 1648755

Reaction equation

HRID 1648755 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[S:17](Cl)Cl.C(N([CH2:25][CH3:26])CC)C.[NH:27]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:28][C:29]([O-:31])=[O:30]>C(Cl)(Cl)Cl>[CH2:36]([O:35][C:33]([CH2:32][N:27]([CH2:28][C:29]([O:31][CH2:25][CH3:26])=[O:30])[S:17][N:2]([CH3:1])[C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:34])[CH3:37]

Participants

6

Reactant 4

HCID 2566CarbofuranHCID 8471Triethylamine2×HCID 25353Sulfur dichlorideHCID 18321666Ethyl iminodiacetate

Product 1

HCID 3067956Glycine, N-(((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(2-ethoxy-2-oxoethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A 11 g quantity (0.05 mole) of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate was dissolved in 50 ml of chloroform, 5.2 g (0.05 mole) of sulfur dichloride was added to the solution with cooling, and 5 g (0.05 mole) of triethylamine was further added dropwise to the solution at 0° C. The mixture was stirred at the same temperature for 2 hours, a solution of 9.5 g (0.05 mole) of ethyl iminodiacetate in 20 ml of chloroform was then added dropwise to the mixture at the same temperature, and 5 g (0.05 mole) of triethylamine was further added dropwise to the mixture. The resulting mixture was stirred at 0° C. for 2 hours and thereafter allowed to stand overnight at room temperature. With addition of 100 ml of chloroform, the reaction mixture was washed with 100 ml of water three times. The chloroform layer was dried and then concentrated in a vacuum to give an oily product, which was almost entirely composed of the desired product although containing small amounts of the starting materials. Yield: 15.9 g (72.3%).

Workup

  1. temperaturewith cooling
  2. additionwas further added dropwise to the mixture
  3. stirringThe resulting mixture was stirred at 0° C. for 2 hours
  4. waitto stand overnight at room temperature
  5. washthe reaction mixture was washed with 100 ml of water three times
  6. dry with materialThe chloroform layer was dried
  7. concentrationconcentrated in a vacuum
  8. customto give an oily product, which

Sources & evidence

ORD record
ord-9e5d27a709114dab95248d07b91ab153
Source dataset
uspto-grants-1983_11
Patent number
US04413005

Linked notes

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