2-Chloroethyl isocyanate → HCID 90426655, compound

HRID 2278985Notes

Reaction equation

HRID 2278985 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH:6]([NH2:8])[CH2:5][CH2:4][O:3]1.[Cl:10][CH2:11][CH2:12][N:13]=[C:14]=[O:15]>C1COCC1>[Cl:10][CH2:11][CH2:12][NH:13][C:14]([NH:8][CH:6]1[CH2:5][CH2:4][O:3][C:2]([CH3:9])([CH3:1])[CH2:7]1)=[O:15]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanate2×HCID 38092032,2-dimethyltetrahydro-2H-pyran-4-amine

Product 1

HCID 90426655HCID 90426655, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. suspension of 2,2-dimethyltetrahydro-2H-pyran-4-amine (0.806 g, 6.24 mmol) in THF (30 mL) was treated drop-wise with 2-chloroethyl isocyanate (0.585 mL, 6.86 mmol), allowed to warm to RT as the cooling bath expired and stirred overnight. The mixture was treated with additional 2-chloroethyl isocyanate (160 μL) and stirred at RT for an additional 24 hours, then concentrated to dryness, the residue dissolved in EtOAc and washed with saturated NH4Cl (1×), NaHCO3 (1×) and brine (1×), dried over MgSO4 and concentrated to dryness to afford 1-(2-chloroethyl)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)urea (700 mg, 48%) as a yellow oil. MS (ESI) m/z: 235.1 (M+H+).

Workup

  1. stirringstirred at RT for an additional 24 hours
  2. concentrationconcentrated to dryness
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with saturated NH4Cl (1×), NaHCO3 (1×) and brine (1×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0f7a851bf49e4c95bcf7f8f2c5bc8aa8
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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