Methyl iodide → HCID 13126000, compound

HRID 1112102Notes

Reaction equation

HRID 1112102 reaction equation
[H-].[Na+].[F:3][CH:4]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[C:8]2[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:7]=2[NH:6][C:5]1=[O:23].[CH3:24]I>O1CCCC1>[F:3][CH:4]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[C:8]2[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:7]=2[N:6]([CH3:24])[C:5]1=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13125992HCID 13125992, compound

Product 1

HCID 13126000HCID 13126000, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of 0.17 g (0.007 mole) of sodium hydride in 10 ml of tetrahydrofuran was added to a solution of 1.8 g (0.005 mole) of 3-fluoro-7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one and 10 ml methyl iodide in 100 ml tetrahydrofuran. The reaction mixture was stirred for 3 hr at 25° and then poured into 300 ml ice water. The aqueous mixture was extracted with methylene chloride, and the extracts were dried (MgSO4) and then evaporated to dryness under reduced pressure. The residue was recrystallized from heptane to give 0.91 g (50%) of cream-colored crystals: mp 127°-130° (with previous softening); 1H nmr (CDCl3) δ 3.49 ppm (s, 3H), 5.62 ppm (d, J = 57 Hz, 1H) and 6.9-7.9 ppm (m, 7H); 19F nmr (CDCl3) δ -111.9 ppm (m, 1F) and -162.4 ppm (d, J = 57 Hz, 1F).

Workup

  1. extractionThe aqueous mixture was extracted with methylene chloride
  2. dry with materialthe extracts were dried (MgSO4)
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-ddab0329d842433794b1d9c9aa34ec65
Source dataset
uspto-grants-1978_10
Patent number
US04120856

Reaction notes

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