Dimethylformamide → HCID 22175022, compound

HRID 1864514Notes

Reaction equation

HRID 1864514 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[NH:12]C(=O)[O:10][C:8](=O)[C:7]2=[CH:14][CH:15]=1)([O-:3])=[O:2].[Cl:16][C:17]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:18]=1[CH2:19][CH2:20][NH2:21].CN(C=O)C>C(Cl)Cl>[NH2:12][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]=1[C:8]([NH:21][CH2:20][CH2:19][C:18]1[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:17]=1[Cl:16])=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1429382,4-DichlorophenethylamineHCID 2820894-Nitro-isatoic anhydride

Product 1

HCID 22175022HCID 22175022, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-nitro-isatoic anhydride (10.0 g, 0.048 mol) in CH2Cl2 (100 mL) was added 2,4-dichlorophenethylamine (10.08 g, 0.053 mol) followed by DMF (10 mL). The reaction mixture was stirred at room temperature for 30 min. The resulting mixture was then dissolved in 1.0 L CH2Cl2 and washed with 1.0 M NaOH. The combined organic layers were concentrated under reduced pressure and purified by silica gel flash chromatography (0-100% EtOAc/hexanes eluent) to give the product (16.5 g, 97% yield) as a yellow solid. HPLC retention time: 3.04 min; Method A; LRMS (ESI) m/z 354 (M+1).

Workup

  1. washwashed with 1.0 M NaOH
  2. concentrationThe combined organic layers were concentrated under reduced pressure
  3. custompurified by silica gel flash chromatography (0-100% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-b8c5839c270d4db4b7c20a7d7d8a59f3
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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