Diethyl Ether → HCID 19432958, compound

HRID 1736415Notes

Reaction equation

HRID 1736415 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[CH:4][N:3]=1.[CH3:19][S-:20].[Na+].C(OCC)C>CN(C)C=O>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([S:20][CH3:19])=[N:3][CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4378561Sodium methanethiolateHCID 19365952HCID 19365952, compound

Product 1

HCID 19432958HCID 19432958, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product of part (ii) (23.9 g, 89 mmol) in N,N-dimethylformamide (DMF) (105 ml) was treated with sodium methanethiolate (6.6 g, 94 mmol) and the resulting suspension was stirred for 2 hours at room temperature. The mixture was poured into diethyl ether (1000 ml) and the suspension was washed with water (2×500 ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was triturated with diethyl ether to afford the title compound as a yellow solid, (3.3 g).

Workup

  1. washthe suspension was washed with water (2×500 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-9adc2433ff24476980274b7ad2ef83c5
Source dataset
uspto-grants-1996_07
Patent number
US05541203

Reaction notes

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