Triethylamine → HCID 86719519, compound

HRID 1772281Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][NH2:11])=[CH:7][C:6]=2[CH:12]=1.C(N(CC)CC)C.Cl[C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][NH:11][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:27])=[CH:7][C:6]=2[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (5-chloro-1-benzofuran-2-yl)methanamine (420 mg, crude) in dichloromethane (50 ml) was added triethylamine (315 mg, 3.12 mmol). Then ethyl 2-chloro-2-oxoacetate (378 mg, 2.77 mmol) was added dropwise and the contents were stirred for 30 minutes at 0° C. The resulting solution was quenched with water (100 ml) and extracted with dichloromethane (3×70 ml). The organic fractions were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with 20% ethyl acetate in petroleum ether to afford ethyl [[(5-chloro-1-benzofuran-2-yl)methyl]carbamoyl]formate as an off-white solid (600 mg). (ES, m/z): [M+H]+ 282.0; 1H NMR (400 MHz, CDCl3): δ 7.52 (s, 2H), 7.38 (d, J=8.4 Hz, 1H), 7.26 (d, J=8.8 Hz, 1H), 6.64 (s, 1H), 4.68 (d, J=4.2 Hz, 2H), 4.39 (q, J=7.2 Hz, 2H), 1.37 (t, J=7.2 Hz, 3H).

Workup

customThe resulting solution was quenched with water (100 ml)
extractionextracted with dichloromethane (3×70 ml)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by silica gel column chromatography
washeluting with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-b5faeac521f840f0afb7229addcf00b5
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249102B2

Reaction notes

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