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.[CH2:17]([N:21]([CH2:24][CH2:25][CH2:26][CH3:27])[S:22]Cl)[CH2:18][CH2:19][CH3:20].N1C=CC=CC=1.O>CCCCCC>[CH2:17]([N:21]([CH2:24][CH2:25][CH2:26][CH3:27])[S:22][CH2:1][NH:2][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)[CH2:18][CH2:19][CH3:20]Participants
Conditions
- Temperature
- 35 °C
Procedure
A flask was charged with 15.8 g of 98% 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (0.07 mole) and 30.2 g of a 50% solution of dibutylaminosulfenyl chloride (0.077 mole) in hexane under nitrogen atmosphere. To this was added with stirring 7.5 g (0.0455 mole) of triethylamine/sulfur dioxide complex prepared as described in Example 3. Pyridine (6.1 g, 0.077 mole) was then added dropwise with stirring over a period of 16 minutes. The temperature increased from 20.5° C. to 23.5° C. Stirring was continued for three hours after the beginning of pyridine addition during which external heating was supplied to maintain a temperature of 35° C. The mixture was cooled to 10.5° C. and 31 ml of water was added. The mixture was filtered, separated, and the organic layer was concentrated to yield 18.99 g of 75% (by hplc) 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate (53% chemical yield based on the starting carbamate).
Workup
- additionTo this was added
- customprepared
- stirringwith stirring over a period of 16 minutes
- temperatureThe temperature increased from 20.5° C. to 23.5° C
- stirringStirring
- temperatureexternal heating
- temperatureThe mixture was cooled to 10.5° C.
- filtrationThe mixture was filtered
- customseparated
- concentrationthe organic layer was concentrated
Sources & evidence
- ORD record
- ord-9fe424e840554807aea5eae3ee504af8
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04329293
Linked notes
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