Carbofuran → Carbamic acid, methyl((4-methylphenyl)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

HRID 1973394Notes

Reaction equation

HRID 1973394 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:25])[O:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:20][C:21]([NH:23][CH3:24])=[O:22])[CH2:12]1>N1C=CC=CC=1>[CH3:24][N:23]([S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:21](=[O:22])[O:20][C:17]1[C:18]2[O:19][C:11]([CH3:10])([CH3:25])[CH2:12][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 2566CarbofuranHCID 11019146p-Toluenesulfenyl chloride

Product 1

HCID 39691Carbamic acid, methyl((4-methylphenyl)thio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 8.75 g of 4-methylbenzenesulfenyl chloride in 25 ml of pyridine was added to a solution of 10.9 g of carbofuran in 25 ml of pyridine. A precipitate formed immediately. The reaction mixture was processed as described in Example I to give a residue which could not be distilled even at 0.005 mm. Passage through a falling film still at 140° at 0.01 mm, then at 168° at 0.01 mm gave a liquid which crystallized on standing to a solid, m.p. 62°. Recrystallization several times from petroleum ether gave 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(4-methylphenylthio)carbamate, m.p. 65°.

Workup

  1. customA precipitate formed immediately
  2. customto give a residue which could not
  3. distillationbe distilled even at 0.005 mm
  4. customPassage through a falling film still at 140° at 0.01 mm, then at 168° at 0.01 mm gave a liquid which
  5. customcrystallized
  6. customRecrystallization several times from petroleum ether

Sources & evidence

ORD record
ord-901f9e8ab5fa4dacb42a056ce2c7797d
Source dataset
uspto-grants-1976_12
Patent number
US03997549

Reaction notes

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