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

HRID 1648754Notes

Reaction equation

HRID 1648754 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]([CH2:31][C:32]#[N:33])[CH2:28][C:29]#[N:30]>C(Cl)Cl.O1CCCC1>[C:29]([CH2:28][N:27]([CH2:31][C:32]#[N:33])[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:30]

Participants

7

Reactant 4

HCID 2566CarbofuranHCID 8471Triethylamine2×HCID 25353Sulfur dichlorideHCID 69413Iminodiacetonitrile

Product 1

HCID 3067955Carbamic acid, ((bis(cyanomethyl)amino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 11 g quantity (0.05 mole) of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate was dissolved in 70 ml of methylene chloride, 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 4.8 g (0.05 mole) of iminodiacetonitrile in 40 ml of tetrahydrofuran 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 4 hours and thereafter allowed to stand overnight at room temperature. With addition of 100 ml of methylene chloride, the reaction mixture was washed with 100 ml of water three times. The methylene chloride 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: 13.8 g (79.8%).

Workup

  1. temperaturewith cooling
  2. additionwas further added dropwise to the mixture
  3. stirringThe resulting mixture was stirred at 0° C. for 4 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 methylene chloride layer was dried
  7. concentrationconcentrated in a vacuum
  8. customto give an oily product, which

Sources & evidence

ORD record
ord-d1aeffa2ed024821944bfe10d8474586
Source dataset
uspto-grants-1983_11
Patent number
US04413005

Reaction notes

Loading…