Dimethylcarbamoyl Chloride → HCID 67182967, compound

HRID 1966446Notes

Reaction equation

HRID 1966446 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O-:3])=[O:2].[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26].C(N(CC)CC)C>ClCCl>[CH3:23][N:24]([CH3:28])[C:25]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:6]=2)[CH2:11][CH2:12]1)=[O:26]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 58425618HCID 58425618, compound

Product 1

HCID 67182967HCID 67182967, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-nitro-N-phenyl-5-(piperazin-1-yl)benzenamine (0.30 g, 1.0 mmol), dimethylcarbamic chloride (0.09 ml, 1.0 mmol) and triethylamine (0.16 ml, 2.0 mmol) in 20 ml dichloromethane was stirred at 0° C. for 2 hours. The mixture was washed with water (2×10 ml) and dried over anhydrous sodium sulfate before removing the solvents. 5-(4-dimethylcarbamylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (0.35 g, 95%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 2.88 (s, 6H), 3.31 (dd, J=1.5, 6.4 Hz, 4H), 3.42 (dd, J=1.5, 6.4 Hz, 4H), 6.34 (dd, J=2.6, 9.6 Hz, 1H), 6.41 (d, J=2.6 Hz, 1H), 7.26-7.47 (m, 5H), 8.17 (d, J=9.6 Hz, 1H), 9.88 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 38.9, 46.6, 47.0, 60.9, 96.5, 106.2, 125.0, 126.0, 129.4, 130.2, 139.4, 145.9, 156.0, 164.8.

Workup

  1. washThe mixture was washed with water (2×10 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. custombefore removing the solvents

Sources & evidence

ORD record
ord-6c5c9571aa0e4f2388e99aa7f27c713f
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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