2-Chloroethyl isocyanate → Urea, 1-(2-chloroethyl)-3-(2-indanyl)-

HRID 1876701Notes

Reaction equation

HRID 1876701 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C(N(CC)C(C)C)(C)C.[Cl:21][CH2:22][CH2:23][N:24]=[C:25]=[O:26]>C(#N)C>[Cl:21][CH2:22][CH2:23][NH:24][C:25]([NH:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)=[O:26]

Participants

5

Reactant 3

HCID 160352-Chloroethyl isocyanateHCID 81531DiisopropylethylamineHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 96888Urea, 1-(2-chloroethyl)-3-(2-indanyl)-Yield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized according to general procedure 40. The reaction was set up with 2-aminoindan hydrochloride (5.0 g, 29.5 mmol), N,N-diisopropylethylamine (10.3 mL, 58.9 mmol), acetonitrile (100 mL), and 2-chloroethylisocyanate (2.52 mL, 29.5 mmol). Purification via silica gel chromatography using 50% EtOAc in hexanes gave the desired urea as a white solid (3.3 g, 13.8 mmol, 47% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.23-7.18 (m, 2H), 7.15-7.11 (m, 2H), 6.38 (d, J=7.3 Hz, 1H), 6.03 (t, J=5.7 Hz, 1H), 4.36-4.28 (m, 1H), 3.57 (t, J=6.2 Hz, 2H), 3.38-3.29 (m, 2H), 3.12 (dd, J=7.1, 15.8 Hz, 2H), 2.68 (dd, J=5.5, 15.8 Hz, 2H).

Workup

  1. customSynthesized
  2. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-6d1823004d9a4b0eb73fa7017d063bde
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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