Bis(2-chloroethyl) ether → HCID 70913381, compound

HRID 1844750Notes

Reaction equation

[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=3)=[CH:11][C:10]([S:27]([NH2:30])(=[O:29])=[O:28])=[C:9]2[CH3:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:35][CH2:36][O:37][CH2:38][CH2:39]Cl>CN(C=O)C>[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=[C:15]([C:23]([CH3:24])([CH3:25])[CH3:26])[CH:14]=3)=[CH:11][C:10]([S:27]([N:30]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)(=[O:29])=[O:28])=[C:9]2[CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 1 (300 mg, 0.68 mmol) in dry DMF (5 mL) was added NaH (60%, 60 mg, 1.50 mmol) at 0° C. and the mixture was stirred at 0° C. for 10 min. 2-chloro-1-(2-chloroethoxy)ethane (97 mg, 0.68 mmol) and KI (113 mg, 0.68 mmol) was added and then this mixture was stirred overnight at rt, quenched with water and extracted with EA. The organic layer was washed with brine twice, concentrated and purified by CC (PE/EA=4/1) to give compound 44 (70 mg, 21%) as a white solid. 1H-NMR (CDCl3, 300 MHz) δ: 0.60-0.70 (2H, m), 0.95-1.03 (3H, m), 1.23-1.40 (3H, m), 1.36 (18H, s), 1.49-1.52 (3H, m), 2.52 (3H, s), 3.02-3.05 (4H, m), 3.73-3.78 (6H, m), 6.35 (1H, s), 7.15 (2H, d, J=1.8 Hz), 7.41 (1H, t, J=1.8 Hz). MS Calcd.: 514; MS Found: 515 (M+1).

Workup

stirringthis mixture was stirred overnight at rt
customquenched with water
extractionextracted with EA
washThe organic layer was washed with brine twice
concentrationconcentrated
custompurified by CC (PE/EA=4/1)

Sources & evidence

ORD record: ord-d7d9dc6c5ff4456b899d6e6605dd8a30
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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