Water → 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (4-tert-butylphenylthio)(methyl)carbamate

HRID 1973393Notes

Reaction equation

HRID 1973393 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][C:14]1([CH3:28])[O:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[O:23][C:24]([NH:26][CH3:27])=[O:25])[CH2:15]1.O>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11][N:26]([CH3:27])[C:24](=[O:25])[O:23][C:20]2[C:21]3[O:22][C:14]([CH3:13])([CH3:28])[CH2:15][C:16]=3[CH:17]=[CH:18][CH:19]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2566CarbofuranHCID 12801136p-t-Butylbenzenesulfenyl chloride

Product 1

HCID 236207882,3-Dihydro-2,2-dimethyl-7-benzofuranyl (4-tert-butylphenylthio)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

One-half (by volume) of the resultant solution of 4-(tert-butyl)benzenesulfenyl chloride was added to a solution of 10.9 g of carbofuran in 30 ml of pyridine. The mixture was allowed to stand overnight, then poured into water. The water-insoluble material was washed several times with water, then dissolved in ether. The ether solution was washed with water and dried. Removal of the ether under reduced pressure gave a solid which on recrystallization from hexane-ether gave 7.5 g of solid, m.p. 120°-3°. Four recrystallizations from hexane gave 2,3-dihydro-2,2-dimethyl-7-benzofuranyl [4-(tert-butyl)phenylthio] (methyl)carbamate, m.p. 122°-123°. The n.m.r. spectrum was consistent with the assigned structure.

Workup

  1. washThe water-insoluble material was washed several times with water
  2. dissolutiondissolved in ether
  3. washThe ether solution was washed with water
  4. customdried
  5. customRemoval of the ether under reduced pressure
  6. customgave a solid which
  7. customon recrystallization from hexane-ether

Sources & evidence

ORD record
ord-2d1f6b4559d640b09a5d2239f2d158b2
Source dataset
uspto-grants-1976_12
Patent number
US03997549

Reaction notes

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