2-Methylbenzylamine → HCID 11652890, compound

HRID 645528Notes

Reaction equation

HRID 645528 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[Cl:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[N:18]=[C:19]=S.[N-:21]=[N+:22]=[N-:23].[Na+]>C1COCC1>[Cl:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[N:18]1[C:19]([NH:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[CH3:1])=[N:23][N:22]=[N:21]1

Participants

5

Reactant 3

HCID 69932-MethylbenzylamineHCID 33557Sodium AzideHCID 27962812,3-Dichlorophenyl Isothiocyanate

Product 1

HCID 11652890HCID 11652890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methylbenzylamine (89.1 mg, 0.735 mmol) in 8 ml of dry THF was treated with 2,3-dichlorophenylisothiocyanate (150 mg, 0.735 mmol). After stirring at room temperature for 1 hour, the mixture was treated with mercuric acetate (234.2 mg, 0.735 mmol) and sodium azide (143.3 mg, 2.21 mmol) and stirred at room temperature for 16 hours. The mixture was filtered through a pad of Celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile to ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/min to provide the title compound. MS (ESI+) m/z 334 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (s, 3H), 4.46 (d, J=5.42 Hz, 2H), 7.16 (m, 3H), 7.26 (m, 1H), 7.57 (t, J=5.42 Hz, 1H), 7.60 (t, J=8.14 Hz, 1H), 7.71 (dd, J=7.97, 1.53 Hz, 1H), 7.93 (dd, J=8.14, 1.70 Hz, 1H).

Workup

  1. stirringstirred at room temperature for 16 hours
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)
  6. customover 15 minutes

Sources & evidence

ORD record
ord-df1e42b9614a438693729f25fe0b9277
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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