Methyl iodide → Benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamate

HRID 2061056Notes

Reaction equation

HRID 2061056 reaction equation
[SH:1][CH2:2][C:3]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])[CH3:4].[CH3:17]I>CO>[CH3:4][C:3]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])[CH2:2][S:1][CH3:17]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59614731Benzyl 1-mercapto-2-methylpropan-2-ylcarbamate

Product 1

HCID 60134425Benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamateYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a pressure tube was added a solution of benzyl 1-mercapto-2-methylpropan-2-ylcarbamate in methanol (5 mL), TEA (2.35 mL, 1 equiv) and methyl iodide (1.05 mL, 1 equiv). The tube was sealed and the reaction stirred for 17 h. The solvent was removed in vacuo and the crude material was purified on an ISCO purification system. The desired fractions were pooled and concentrated under reduced pressure to give a pale yellow oil (2.78 g, 65%). 1H NMR (CDCl3, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2 H). LRMS (ESI+) for C13H19NO2S (253.1); Found: 254 (MH+).

Workup

  1. customThe tube was sealed
  2. customThe solvent was removed in vacuo
  3. customthe crude material was purified on an ISCO purification system
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a0ca889ea0c462fbc4c09bc093cff08
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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