Methyl iodide → HCID 53760192, compound

HRID 1277342Notes

Reaction equation

HRID 1277342 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]#[N:8].[CH:9]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:29]([O:31][C:32](=[O:37])[CH:33]=[CH:34][CH2:35][F:36])[CH3:30].CI.[Cl-].[NH4+]>O1CCCC1>[CH2:29]([O:31][C:32](=[O:37])[CH:33]([CH3:9])[CH:34]([C:2]1([C:7]#[N:8])[S:3][CH2:4][CH2:5][CH2:6][S:1]1)[CH2:35][F:36])[CH3:30]

Participants

9

Reactant 7

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 9728HCID 9728, compoundHCID 25517Ammonium ChlorideHCID 3118391,3-dithiane-2-carbonitrileHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 53760192HCID 53760192, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 1.45 g (10 mMole) of 1,3-dithian-2-carbonitrile in 10 ml of tetrahydrofuran is added to lithium diisopropylamide, prepared from diisopropylamine (1.01 g, 10 mMole) and butyllithium (4.8 ml of a 2.1 M solution, 10 mM) in 20 ml of tetrahydrofuran at -70° C. To the solution is added 1.25 g (9,5 mMole) of 3-monofluoromethylacrylic acid ethyl ester in 5 ml of tetrahydrofuran and the reaction mixture is stirredat -70° C. for 30 minutes after which 1.3 g (10 mMole) of methyl iodide is added and the mixture is maintained at 0° C. for 15 hours, then poured into aqueous ammonium chloride and extracted with ether. The ether solution is dried and evaporated to give the title compound.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether solution is dried
  3. customevaporated

Sources & evidence

ORD record
ord-4111cf2876f04d50b243b775774c20af
Source dataset
uspto-grants-1981_07
Patent number
US04277395

Reaction notes

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