Dichloromethane → HCID 89540102, compound

HRID 1022004Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:20](=[O:21])[C:19]3[S:18][C:17]4[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=4[C:11]=3[CH:10]=[N:9]2)[C:3]=1[CH2:22][OH:23].ClCCl.[C:27](Cl)(=[O:29])[CH3:28]>C(N(CC)CC)C>[C:27]([O:23][CH2:22][C:3]1[C:4]([N:8]2[C:20](=[O:21])[C:19]3[S:18][C:17]4[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=4[C:11]=3[CH:10]=[N:9]2)=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

A round-bottomed flask was charged with 230g (597 mg, 1.72 mmol), dichloromethane (50 mL), and triethylamine (5 mL). The solution was stirred at 0° C. for 0.5 h and acetyl chloride (135 mg, 1.72 mmol) was added slowly. The mixture was stirred at 0° C. for another 2.5 h. It was then concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 9:1 petroleum ether/ethyl acetate to afford 230h (602 mg, 90%) as a yellow solid. MS-ESI: [M+H]+ 390.1

Workup

stirringThe mixture was stirred at 0° C. for another 2.5 h
concentrationIt was then concentrated under reduced pressure
customThe residue was purified by silica-gel column chromatography
washeluting with 9:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record: ord-124dab38a7444ceca82acb98ca562184
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716274B2

Reaction notes

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