Sodium Sulfide → HCID 58191367, compound

HRID 1918220Notes

Reaction equation

HRID 1918220 reaction equation
Cl[CH2:2][C:3](=[O:19])[C:4](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([F:17])[C:11]=1[F:18])[C:5]([O:7][CH3:8])=[O:6].[S-2:20].[Na+].[Na+]>CO>[F:18][C:11]1[C:12]([F:17])=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[CH:9]1[CH:4]([C:5]([O:7][CH3:8])=[O:6])[C:3](=[O:19])[CH2:2][S:20]1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 76720152HCID 76720152, compound

Product 1

HCID 58191367HCID 58191367, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Compound 371 (18.7 g, 65 mmol) suspended in anhydrous methanol (50 ml) was added slowly to a solution of dry sodium sulfide (10.0 g, 129 mmol) in methanol (50 ml) while keeping the internal temperature below 40° C. The solution was stirred for 1 h at room temperature then quenched by pouring into a rapidly stirred mixture of ice (350 ml) and 2M HCl (200 ml). The mixture was extracted with dichloromethane (3×250 ml) and the combined extracts dried with brine (100 ml) then sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-30% ethyl acetate in hexane) provided 372 (12.2 g, 66%) as a crystalline solid.

Workup

  1. customthe internal temperature below 40° C
  2. customthen quenched
  3. additionby pouring into a rapidly stirred mixture of ice (350 ml) and 2M HCl (200 ml)
  4. extractionThe mixture was extracted with dichloromethane (3×250 ml)
  5. dry with materialthe combined extracts dried with brine (100 ml)
  6. concentrationsodium sulfate and concentrated under reduced pressure

Sources & evidence

ORD record
ord-c65e28d6aa2a49fe8439f70709069205
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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