2-Chloroethyl isocyanate → N'-(2-Chloroethyl)-N-(2,3-dihydro-1H-inden-5-yl)carbamimidic acid

HRID 1289635Notes

Reaction equation

HRID 1289635 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[Cl:11][CH2:12][CH2:13][N:14]=[C:15]=[O:16]>C(OCC)C>[Cl:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 90496Indan-5-amine

Product 1

HCID 294116N'-(2-Chloroethyl)-N-(2,3-dihydro-1H-inden-5-yl)carbamimidic acidYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2 g of 5-aminoindane in 125 mL of anhydrous ethyl ether was added dropwise, 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 16 h at room temperature, cooled at -20° C., and filtered. A white solid separated and was recrystallized from ethanol (white flakes), yield 40%, mp 155°-157° C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1H NMR (DMSO-d6 : CDCl3): 6.96 ppm, 3.52 ppm, 3.49 ppm, 3.46 ppm, 3.43 ppm, 2.74 ppm, 2.72 ppm, 1.93 ppm. In this spectrum hydrogen present on NH groups have exchanged with the presence of DMSO-d6.

Workup

  1. temperaturecooled at -20° C.
  2. filtrationfiltered
  3. customA white solid separated
  4. customwas recrystallized from ethanol (white flakes), yield 40%, mp 155°-157° C., IR (KBr pellet)

Sources & evidence

ORD record
ord-471db42d6b53427b8711c7fe007ec97b
Source dataset
uspto-grants-1998_05
Patent number
US05750547

Reaction notes

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