Carbofuran → Carbamic acid, (((2-cyanoethyl)(1-methylethyl)amino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

HRID 905002Notes

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.[CH:17]([N:20]([CH2:23][CH2:24][C:25]#[N:26])[S:21]Cl)([CH3:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[CH:17]([N:20]([CH2:23][CH2:24][C:25]#[N:26])[S:21][N:2]([CH3:1])[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)([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

2.2 g (0.01 mole) of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate and 1.8 g (0.01 mole) of N-isopropyl-N-cyanoethylaminosulfenyl chloride were dissolved in 30 ml of methylene chloride, and the solution was cooled to 0° C. 1.2 g (0.012 mole) of triethylamine was dropwise added thereto with stirring, and allowed to react for 2 hours at the same temperature. After completion of the reaction, the reaction solution was washed successively with water, diluted hydrochloric acid and water. The methylene chloride layer was dried and concentrated under reduced pressure to obtain an oily product which was almost entirely composed of the desired product although containing small amounts of the starting materials and impurities.

Workup

customto react for 2 hours at the same temperature
customAfter completion of the reaction
washthe reaction solution was washed successively with water, diluted hydrochloric acid and water
dry with materialThe methylene chloride layer was dried
concentrationconcentrated under reduced pressure
customto obtain an oily product which

Sources & evidence

ORD record: ord-4485cd3536974ccf95a35204c07b2742
Source dataset: uspto-grants-1983_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04421693

Reaction notes

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