Hydrochloric Acid → HCID 114463720, compound

HRID 632536Notes

Reaction equation

Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([OH:10])[CH3:9].[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH2:15].C(N(CC)CC)C.Cl>ClCCl>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH:15][S:2]([NH:5][C:6](=[O:7])[O:10][CH2:8][CH3:9])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of chlorosulfonylisocyanate (11.32 g, 80 mmol) in dichloromethane (120 mL) was cooled to 0° C. Ethanol (4.67 mL, 80.0 mmol, 1.0 equiv.) was added via addition funnel. The mixture was stirred at 0° C. for 1.5 h. To this mixture was added a solution of aminoacetaldehyde dimethyl acetal (8.76 mL, 80.0 mmol, 1.0 equiv.), triethylamine (TEA, 33.4 mL, 240 mmol, 3.0 equiv.) in dichloromethane (DCM, 120.0 mL) drop-wise via addition funnel 0° C. The reaction was warmed to room temperature and stirred overnight. The reaction was treated with 0.1 N hydrochloric acid and the collected organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuum to give the desired product (11.2 g, 55%) as a crude off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.13 (s, 1H), 7.81 (t, 1H, J=6.0 Hz), 4.37 (t, 1H, J=5.5 Hz), 4.09 (q, 2H, J=7.1 Hz), 3.23 (s, 6H), 2.97 (dd, 2H, J=5.8 Hz), 1.19 (t, 3H, J=7.1 Hz).

Workup

additionvia addition funnel 0° C
temperatureThe reaction was warmed to room temperature
stirringstirred overnight
washthe collected organic phase was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-e7f8ad6932fa475bb66f5fbd23a8782a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321755B2

Reaction notes

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