Triethylamine → 3-[(N-methylureido)tridecyl]-5-Trimethylsilylfuran

HRID 1109877Notes

Reaction equation

HRID 1109877 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].N[CH:6]([C:19]1[CH:23]=[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])[O:21][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([N:30](CC)CC)C>ClCCl>[CH3:1][N:2]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:19]1[CH:23]=[C:22]([Si:24]([CH3:26])([CH3:27])[CH3:25])[O:21][CH:20]=1)[C:3]([NH2:30])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 150370773-(1-Aminotridecyl)-5-trimethylsilylfuran

Product 1

HCID 543511783-[(N-methylureido)tridecyl]-5-Trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methylisocyanate (23 ul, 0.38 mmol) in dichloromethane (0.5 ml) was added to a solution of 3-(1-aminotridecyl)-5-trimethylsilylfuran (85.5 mg, 0.25 mmol) and triethylamine (53 microliter, 0.3 mmol) in dichloromethane (2 ml) at room temperature. Stirring was continued for two days and the reaction mixture was quenched with water. Extraction (dichloromethane) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by preparative TLC (20×20 CM, 1000ul; developed with 40% ethyl acetate/hexane) to give the titled urea as a colorless oil.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionExtraction (dichloromethane) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave an oil, which
  5. customwas purified by preparative TLC (20×20 CM, 1000ul; developed with 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-af7e15c338614ba68ac1ec6e8748dd56
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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