Isopropyl isocyanate → Tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate

HRID 62685

Reaction equation

HRID 62685 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[CH:21]([N:24]=[C:25]=[O:26])([CH3:23])[CH3:22]>ClCCl.O>[CH:21]([NH:24][C:25](=[O:26])[NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 71007316Tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamateYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (0.20 g, 0.70 mmol, 1.0 equiv.) in dichloromethane (4 mL) was added isopropyl isocyanate (0.07 mL, 0.83 mmol, 1.2 equiv.) and TEA (0.19 mL, 1.37 mmol) at 0° C. The reaction was stirred at room temperature for 16 h. The reaction was then diluted with dichloromethane and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate, then concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 20% EtOAc/hexanes) to give tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate (0.18 g, 70% yield).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5a8d2f727f2b4103ace43af14fb3d904
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Linked notes

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