Sulfur Dioxide → 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate

HRID 1065214Notes

Reaction equation

S(=O)=O.[CH2:4]([N:8]([CH2:11][CH2:12][CH2:13][CH3:14])[S:9]Cl)[CH2:5][CH2:6][CH3:7].[CH3:15][NH:16][C:17](=[O:30])[O:18][C:19]1[C:27]2[O:26][C:25]([CH3:29])([CH3:28])[CH2:24][C:23]=2[CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>CCCCCC.O>[CH2:4]([N:8]([CH2:11][CH2:12][CH2:13][CH3:14])[S:9][CH2:15][NH:16][C:17](=[O:30])[O:18][C:19]1[C:27]2[O:26][C:25]([CH3:28])([CH3:29])[CH2:24][C:23]=2[CH:22]=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 9.5 °C

Procedure

Sulfur dioxide was passed through 30.2 g of a 50% solution of dibutylaminosulfenyl chloride (0.077 mole) in hexane until the solution had gained 2.8 g (0.044 mole). 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (98%, 15.5 g, 0.069 mole) was added followed by dropwise addition of triethylamine (12.4 g, 0.123 mole) over a period of 28 minutes with stirring. Stirring was continued for about 18 hours. The mixture was cooled to 9.5° C., 31 ml of water and 40 ml of hexane were added, and the layers were separated. The organic layer was concentrated to yield 27.4 g of 94% (by hplc) 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate (98% chemical yield).

Workup

stirringStirring
customthe layers were separated
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-4f7817f34f5a41a79ea7f4d899bf9e84
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04329293

Reaction notes

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