3-Chloro-4-methylphenyl isocyanate → HCID 66784893, compound

HRID 1096590Notes

Reaction equation

HRID 1096590 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:2]1.[Cl:16][C:17]1[CH:22]=[C:21]([N:23]=[C:24]=[O:25])[CH:20]=[CH:19][C:18]=1[CH3:26]>ClCCl>[NH:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:24]([NH:23][C:21]2[CH:20]=[CH:19][C:18]([CH3:26])=[C:17]([Cl:16])[CH:22]=2)=[O:25])[CH2:2]1

Participants

4

Reactant 2

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 53119162-(piperidin-3-yl)-1H-1,3-benzodiazole

Product 1

HCID 66784893HCID 66784893, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(piperidin-3-yl)-1H-benzo[d]imidazole (100.0 mg, 0.497 mmol) was dissolved in dichloromethane (3.0 mL). To the stirred suspension was added 2-chloro-4-isocyanato-1-methylbenzene (84.1 mg, 0.502 mmol). The reaction was stirred at ambient temperature for one hour. The crude mixture was then concentrated in vacuo and the residue was dissolved in minimal amounts of dimethylformamide and purified via preparative HPLC (10%-50% acetonitrile in water). The pure fractions were combines and lyophilized to yield the title compound 1 as a fluffy white solid (147.5 mg, 63.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.65 (m, 1H), 1.83 (d, J=13.73 Hz, 1H), 1.97 (q, 0.1=18.28 Hz, 1H), 2.25 (s, 3H), 2.30 (s, 1H), 2.99 (t, J=11.44 Hz, 1H), 3.23 (t, J=13.34 Hz, 1H), 3.34-3.38 (m, 1H), 4.11 (d, J=13.35 Hz, 1H), 4.48 (d, J=13.35 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.32 (d, J=8.5 Hz, 1H), 7.51-7.34 (m, 1H), 7.63 (s, 1H), 7.78-7.80 (m, 1H), 8.76 (s, 1H), ESI-MS: m/z 369.2 (M+H)+.

Workup

  1. concentrationThe crude mixture was then concentrated in vacuo
  2. dissolutionthe residue was dissolved in minimal amounts of dimethylformamide
  3. custompurified via preparative HPLC (10%-50% acetonitrile in water)

Sources & evidence

ORD record
ord-2df02f7cdb3649169f1684e43e4f1889
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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