Hydrochloric Acid → HCID 68561787, compound

HRID 901185Notes

Reaction equation

HRID 901185 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1.[ClH:16]>CCOC(C)=O.CCCCCC>[Cl:16][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68563567HCID 68563567, compound

Product 1

HCID 68561787HCID 68561787, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of JRL01115 (725 mg, 3.135 mmol) in dichloromethane (10 mL) at ice/water temperature was added thionyl chloride (0.35 mL, 4.703 mmol). After stirring at room temperature for 1 h, the volatiles were removed from the reaction mixture and the oil resulted co-evaporated 3 times with chloroform (3×30 mL) to give to LWO02144 as a yellow oil (767 mg, 98%); Rf 0.52 (EtOAc/hexane, 1:1), c.f. 0.19 (JRL01115); 1H (400 MHz, CDCl3) 2.99 (6H, s, NMe2), 4.58 (2H, s), 7.28 (2H AA′BB′) and 7.42 (2H, AA′BB′); LRMS (FAB+) 403.0 [18, (M+H+NBA)+], 391.2 (21), 249.9 [100, (M+H)+], 214.0 [45, (M+H—Cl)+], 113.0 (17); HRMS (FAB+) 249.02239, C9H12ClNO3S requires 249.02264. LWO02144 was very pure and hence was used without further purification.

Workup

  1. customhence was used without further purification

Sources & evidence

ORD record
ord-24efb70abf5a47dab7515cc2e56fb093
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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