Bis-(2-chloroethyl)sulfide → HCID 89812942, compound

HRID 1480985Notes

Reaction equation

C1CCN2C(=NCCC2)CC1.[C:12]([O:16][C:17](=[O:21])[CH2:18][C:19]#[N:20])([CH3:15])([CH3:14])[CH3:13].Cl[CH2:23][CH2:24][S:25][CH2:26][CH2:27]Cl>CN(C=O)C.CCOC(C)=O>[C:12]([O:16][C:17]([C:18]1([C:19]#[N:20])[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1)=[O:21])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(2-hydroxy-ethylsulfanyl)-ethanol (13.17 g), thionyl chloride (24 mL) in DCM (250 mL) was stirred in an ice/water bath overnight. Then the reaction mixture was concentrated to give crude product 1-chloro-2-(2-chloro-ethylsulfanyl)-ethane (100%), which was used directly in the next step. DBU (42.04 mL) was added slowly to a solution of cyano-acetic acid tert-butyl ester (13.23 g) and 1-chloro-2-(2-chloro-ethylsulfanyl)-ethane (all the crude from previous step) in DMF (200 mL) at rt and then the reaction mixture was stirred in an oil bath (bath temperature=80° C.) overnight. The reaction was cooled, diluted with EtOAc, then washed with cold water, dil. NaCl solution; EtOAc phase was dried over anhydrous sodium sulfate, filtered, concentrated; the residue was column purified to give title compound (7.961 g). 1H NMR in CDCl3, δ in ppm: 3.1-2.9 (m, 2H), 2.7-2.5 (m, 2H), 2.45-2.35 (m, 2H), 2.2-2.1 (m, 2H), 1.51 (s, 9H).

Workup

temperatureThe reaction was cooled
washwashed with cold water, dil. NaCl solution
dry with materialEtOAc phase was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-301ab658ed95442592525086bc2534c6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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