2-Chloroethyl isocyanate → HCID 90427244, compound

HRID 2278939Notes

Reaction equation

HRID 2278939 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH2:6])[CH3:5].[Cl:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12]>C1COCC1>[Cl:7][CH2:8][CH2:9][NH:10][C:11]([NH:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])=[O:12]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 70215362-Propanamine, 1-methoxy-, (2S)-

Product 1

HCID 90427244HCID 90427244, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-1-methoxypropan-2-amine (500 mg, 5.61 mmol) in THF (15 mL) was treated with 2-chloroethylisocyanate (592 mg, 5.61 mmol), stirred at RT overnight, then concentrated to dryness. The residue was treated with toluene and concentrated to dryness (twice) to afford (S)-1-(2-chloroethyl)-3-(1-methoxypropan-2-yl)urea (100% yield assumed) as a white solid which was used without further purification. MS (ESI) m/z: 195.1 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was treated with toluene
  3. concentrationconcentrated to dryness (twice)

Sources & evidence

ORD record
ord-d2ddf7a07f8248d79ec25eea7f74d719
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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