Benzoyl chloride, 3-nitro- → HCID 58958072, compound

HRID 914977Notes

Reaction equation

HRID 914977 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]1[CH2:23][C:24]([NH2:27])([CH3:26])[CH3:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]1[CH2:23][C:24]([NH:27][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:25])[CH3:26]

Participants

6

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 21050991HCID 21050991, compound

Product 1

HCID 58958072HCID 58958072, compoundYield 117%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitrobenzoylchloride (0.14 g, 0.75 mmol) and 43 (0.15 g, 0.76 mmol) in anhydrous CH2Cl2 (7 mL) was added DMAP (10 mg). The reaction was stirred at room temperature overnight before it was diluted with EtOAc (100 mL). Upon sequential washings with 1 N NaOH (2×100 mL), water (200 mL), the organic mixture was dried (Na2SO4) and concentrated under reduced pressure to give 44 (0.31 g,˜100%) as a thick dark oil.

Workup

  1. washUpon sequential washings with 1 N NaOH (2×100 mL), water (200 mL)
  2. dry with materialthe organic mixture was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f15b7f8c66f4d8996c5fe26166a6c09
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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