Triethylamine → 3-Chloro-4,5-dimethoxyphenyl(tosyl)methyl isocyanide

HRID 874721Notes

Reaction equation

[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Cl:24])[CH:15]=2)[NH:11][CH:12]=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>C(COC)OC>[Cl:24][C:16]1[CH:15]=[C:14]([CH:10]([N+:11]#[C-:12])[S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:25])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[CH:19]=[C:18]([O:20][CH3:21])[C:17]=1[O:22][CH3:23]

Participants

Conditions

Temperature: -10 °C

Procedure

Compound 3a (4.57 g, 11.92 mmol) was suspended in dry dimethoxyethane (100 mL) and cooled to −10° C. POCl3 (3.4 mL, 36.1 mmol) was added and a mixture of triethylamine (8.3 mL, 59.5 mmol) in dimethoxyethane (10 mL) was dropped slowly to the reaction mixture. After stirring for 2 h at −5° C., the reaction mixture was poured into ice water. The aqueous phase was extracted with ethyl acetate, the organic phase was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuum. Upon refrigeration (4° C.) over night a yellow solid crystallized, which was collected and dried in vacuum.

Workup

additionwas dropped slowly to the reaction mixture
extractionThe aqueous phase was extracted with ethyl acetate
washthe organic phase was washed with saturated aqueous NaHCO3 and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuum
customUpon refrigeration (4° C.) over night a yellow solid crystallized
customwhich was collected
customdried in vacuum

Sources & evidence

ORD record: ord-23e1971d56e841e99c6a58ea4a429f02
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980933B2

Reaction notes

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