2-Chloroethyl isocyanate → HCID 90426517, compound

HRID 2278944Notes

Reaction equation

HRID 2278944 reaction equation
[CH3:1][O:2][C:3]1([CH2:6][CH2:7][NH2:8])[CH2:5][CH2:4]1.[Cl:9][CH2:10][CH2:11][N:12]=[C:13]=[O:14]>C1COCC1>[Cl:9][CH2:10][CH2:11][NH:12][C:13]([NH:8][CH2:7][CH2:6][C:3]1([O:2][CH3:1])[CH2:5][CH2:4]1)=[O:14]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 838721781455037-17-8

Product 1

HCID 90426517HCID 90426517, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of 2-(1-methoxycyclopropyl)ethanamine (0.361 g, 2.413 mmol) in THF (15 mL) was treated drop-wise with 2-chloroethyl isocyanate (0.226 mL, 2.65 mmol), allowed to warm to RT, stirred overnight, then concentrated to dryness. The residue was treated with toluene and concentrated to dryness (twice) to afford 1-(2-chloroethyl)-3-(2-(1-methoxycyclopropyl)ethyl)urea (429 mg, 81%) as a yellow oil. MS (ESI) m/z: 221.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-4aaa752e2e6643b8b0c943b725977f25
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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