Methyl iodide → HCID 57853869, compound

HRID 1688124Notes

Reaction equation

HRID 1688124 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][C:14](=[S:18])[NH:13][C:12]=2[CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[C:21](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][C:14]([S:18][CH3:21])=[N:13][C:12]=2[CH:19]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57853827HCID 57853827, compound

Product 1

HCID 57853869HCID 57853869, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (2-thioxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-yl)-carbamic acid tert-butyl ester (5.0 g, 17.1 mmol) and potassium carbonate (4.7 g, 34.0 mmol) in acetone (400 mL) was treated with iodomethane (2.5 mL, 5.7 g, 40.0 mmol). The mixture was stirred for 12 h and concentrated. The residue was partitioned between water (100 mL) and DCM (200 mL). The aqueous phase was extracted again with DCM and the combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography with DCM/MeOH (9:1) to give (2-methylsulfanyl-4,5-dihydro-3H-benzo[b]azepin-8-yl)-carbamic acid tert-butyl ester (2.2 g, 7.2 mmol, 42%): 1H NMR (300 MHz, CDCl3) δ 7.1 (m, 3H), 2.92 (t, 1H), 2.81 (t, 1H), 2.55 (s, 3H), 2.4 (q, 2H), 2.32 (q, 2H), 1.6 (s, 9H); MS (m/e) 307 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water (100 mL) and DCM (200 mL)
  3. extractionThe aqueous phase was extracted again with DCM
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography with DCM/MeOH (9:1)

Sources & evidence

ORD record
ord-a0d97db90cdd46d58bd8e2b761269ff9
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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