2-Chloroethyl isocyanate → HCID 60638916, compound

HRID 2278966Notes

Reaction equation

HRID 2278966 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][CH2:6][CH2:7][N:8]=[C:9]=[O:10]>C1COCC1>[Cl:5][CH2:6][CH2:7][NH:8][C:9]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:10]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 69828Cyclopropylamine

Product 1

HCID 60638916HCID 60638916, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopropanamine (0.541 g, 9.48 mmol) in THF (10 mL) was treated with chloroethylisocyanate (1.0 g, 9.48 mmol), stirred at RT for 2 h, then concentrated to dryness and treated with MeCN. The resulting solid was collected via filtration and dried to afford 1-(2-chloroethyl)-3-cyclopropylurea (1.31 g, 85%). 1H NMR (400 MHz, DMSO-d6): δ 6.28 (s, 1 H), 6.12 (br s, 1 H), 3.55 (t, J=6.4 Hz, 2 H), 3.30 (m, 2 H), 2.36 (m, 1 H), 0.55 (m, 2 H), 0.31 (m, 2 H); MS (ESI) m/z: 162.9 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. additiontreated with MeCN
  3. filtrationThe resulting solid was collected via filtration
  4. customdried

Sources & evidence

ORD record
ord-2574a1186d294c83972ac3ce50a71962
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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