Carbofuran → Carbamic acid, ((bis(2-cyanoethyl)amino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

HRID 1648757

Reaction equation

HRID 1648757 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(CC)CC)C.[NH:27]([CH2:32][CH2:33][C:34]#[N:35])[CH2:28][CH2:29][C:30]#[N:31]>C(Cl)(Cl)Cl>[C:30]([CH2:29][CH2:28][N:27]([CH2:32][CH2:33][C:34]#[N:35])[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)#[N:31]

Participants

6

Reactant 4

HCID 2566CarbofuranHCID 81493,3'-IminodipropionitrileHCID 8471Triethylamine2×HCID 25353Sulfur dichloride

Product 1

HCID 3067958Carbamic acid, ((bis(2-cyanoethyl)amino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

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 -10° to -5° C. The mixture was stirred at 0° C. for one hour and further at room temperature for one hour. After cooling to -10° to -5° C., 6.2 g (0.05 mole) of iminodipropionitrile was added dropwise to the mixture, 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 impurities. Yield: 12.2 g (65.2%).

Workup

  1. temperaturewith cooling
  2. temperatureAfter cooling to -10° to -5° C.
  3. additionwas further added dropwise to the mixture
  4. stirringThe resulting mixture was stirred at 0° C. for 2 hours
  5. waitto stand overnight at room temperature
  6. washthe reaction mixture was washed with 100 ml of water three times
  7. dry with materialThe chloroform layer was dried
  8. concentrationconcentrated in a vacuum
  9. customto give an oily product, which

Sources & evidence

ORD record
ord-5a77e36b7c9a400abd60d1dc5c031a7c
Source dataset
uspto-grants-1983_11
Patent number
US04413005

Linked notes

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