Water → Carbamic acid, N-(dimethylamino)thio-N-methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

HRID 435804Notes

Reaction equation

HRID 435804 reaction equation
[CH3:1][C:2]1([CH3:16])[O:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH2:3]1.[CH3:17][N:18]([CH3:21])[S:19]Cl.O>N1C=CC=CC=1>[CH3:17][N:18]([CH3:21])[S:19][N:14]([CH3:15])[C:12](=[O:13])[O:11][C:8]1[C:9]2[O:10][C:2]([CH3:16])([CH3:1])[CH2:3][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2566Carbofuran2×HCID 12297775(Dimethylamino)sulfenyl chloride

Product 1

HCID 41382Carbamic acid, N-(dimethylamino)thio-N-methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 16 g of carbofuran and 8.5 g of (dimethylamino)sulfenyl chloride in 50 ml of pyridine was allowed to stand at room temperature for about 18 hours. The mixture was poured into water, the aqueous mixture extracted with chloroform, the extracts washed with dilute hydrochloric acid, followed by water and saturated sodium chloride solution. Concentration under reduced pressure gave an oil which was found by nuclear magnetic resonance spectroscopy to contain about 20% unreacted carbofuran. This oil was subjected to column chromatography on silica gel using diethyl etherhexane (3:1) as eluting solvent to obtain 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (dimethylaminosulfenyl)(methyl)carbamate

Workup

  1. extractionthe aqueous mixture extracted with chloroform
  2. washthe extracts washed with dilute hydrochloric acid
  3. concentrationConcentration under reduced pressure
  4. customgave an oil which
  5. washas eluting solvent

Sources & evidence

ORD record
ord-a7fe143cb4264d67b770516fccc4a774
Source dataset
uspto-grants-1977_02
Patent number
US04006231

Reaction notes

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