Cyclohexylamine → N-Cyclohexyl-[2,1,3]-benzoxadiazole-5-carboxamide

HRID 238537Notes

Reaction equation

HRID 238537 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:15]1[O:16][N:17]=[C:18]2[CH:23]=[C:22]([C:24](Cl)=[O:25])[CH:21]=[CH:20][C:19]=12>ClCCl>[CH:1]1([NH:7][C:24]([C:22]2[CH:21]=[CH:20][C:19]3=[N:15][O:16][N:17]=[C:18]3[CH:23]=2)=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chloride

Product 1

HCID 25104041N-Cyclohexyl-[2,1,3]-benzoxadiazole-5-carboxamideYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclohexylamine (1 ml) and triethylamine (1.7 ml) in dichloromethane (20 ml) was added a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (730 mg, 4 mmol) in dichloromethane (10 ml). After stirring the mixture for 1 hour, the organic phase was washed with 1N HCl and conc. NaHCO3 solution, dried over magnesium sulfate, and concentrated under vacuum. The residue was triturated with ether to give a white solid (265 mg, yield=27%). Mp=172-173° C., 1H NMR (300 MHz, CDCl3) δ 8.15 (s, 1H), 7.90 (d, 1H, J=9.0 Hz); 7.82 (d, J=9.0 Hz, 1H); 6.09 (“s”, NH, 1H), 4.05-3.97 (m, 1H) and 2.09-1.18 ppm (m, 10H).

Workup

  1. washthe organic phase was washed with 1N HCl and conc. NaHCO3 solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-7cffd6768d0342b9978d0b942e985e60
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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