Chloroform → HCID 86607420, compound

HRID 2111014Notes

Reaction equation

ClC1C=CC=CC=1C([N:10]([C:14]1[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]Cl)=[CH:21][CH:20]=2)=[N:16][O:17][CH:18]=1)[C:11](=[O:13])[O-:12])C.[C:28]([O:32][CH3:33])(=[O:31])[CH2:29][SH:30].C(N([CH2:39][CH3:40])CC)C.[CH:41]([Cl:44])(Cl)Cl>>[Cl:44][C:41]1[CH:20]=[CH:19][CH:15]=[CH:14][C:18]=1[CH:39]([O:12][C:11]([NH:10][C:14]1[C:15]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][S:30][CH2:29][C:28]([O:32][CH3:33])=[O:31])=[CH:23][CH:24]=2)=[N:16][O:17][CH:18]=1)=[O:13])[CH3:40]

Participants

Reactant 4

HCID 6212Chloroform

HCID 8471Triethylamine

HCID 16907Methyl Thioglycolate

HCID 86607421HCID 86607421, compound

Product 1

HCID 86607420HCID 86607420, compoundYield 34%

Conditions

Temperature: 50 °C

Procedure

1-(2-Chlorophenyl)ethyl[3-(4-(2-chloroethyl)phenyl)isoxazolyl]carbamate (481 mg, 1.19 mmol) was dissolved in chloroform (10 ml), methyl thioglycolate (379 mg, 3.57 mmol), and triethylamine (600 mg, 5.93 mmol) were added, and the mixture was stirred overnight at 50° C. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the title compound (190 mg, 34%).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-edc7e0b27a1845e0824369fcb336eb7a
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517996B2

Reaction notes

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