Sodium Hydroxide → 1-{3-[4-(3-Diisobutylamino-propyl)-piperazin-1-yl]-propyl}-3-(4-methoxy-2-nitro-phenyl)-thiourea

HRID 2167070Notes

Reaction equation

HRID 2167070 reaction equation
[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18]C2NC3C=CC=CC=3N=2)[CH2:11][CH2:10]1)[CH:2]([CH3:4])[CH3:3].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[S:42])=[C:36]([N+:43]([O-:45])=[O:44])[CH:35]=1.[OH-].[Na+]>C(Cl)Cl>[CH2:28]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:41]([NH:40][C:37]2[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][C:36]=2[N+:43]([O-:45])=[O:44])=[S:42])[CH2:13][CH2:14]1)[CH:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1410064-Methoxy-2-nitrophenyl isothiocyanateHCID 10252009Ezeprogind2×

Product 1

HCID 873887991-{3-[4-(3-Diisobutylamino-propyl)-piperazin-1-yl]-propyl}-3-(4-methoxy-2-nitro-phenyl)-thiourea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N4-(3-{4-[3-(diisobutylamino)propyl]piperizano}propyl)-amine (intermediate of example 16) (103 mg, 0.33 mmol) and 4-methoxy-2-nitrophenyl isothiocyanate (139 mg, 0.66 mmol) in CH2Cl2 (10 mL) has been stirred for 4 h at room temperature. NaOH 1M is added until alkaline pH. Organic layer was washed with NaOH 0.5M and dried over MgSO4. Crude compound is purified by thick-layer chromatography (CH2Cl2/MeOH: 90/10).

Workup

  1. washOrganic layer was washed with NaOH 0.5M
  2. dry with materialdried over MgSO4
  3. customCrude compound is purified by thick-layer chromatography (CH2Cl2/MeOH: 90/10)

Sources & evidence

ORD record
ord-484929fec2164bb4b63e425b1e006229
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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