4-Nitrobenzoyl chloride → HCID 86585122, compound

HRID 895831Notes

Reaction equation

HRID 895831 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][C:14]1([CH3:29])[O:19][CH2:18][CH:17]([NH:20]C2COC(C)(C)OC2)[CH2:16][O:15]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH3:13][C:14]1([CH3:29])[O:19][CH2:18][CH:17]([NH:20][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:16][O:15]1

Participants

7

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 11334061HCID 11334061, compound

Product 1

HCID 86585122HCID 86585122, compoundYield 100.8%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-Dimethylaminopyridine (20 mg, 0.164 mmol) and 4-nitrobenzoyl chloride (9) (276 mg, 1.49 mmol) were added to a solution of bis-(2,2-dimethyl-1,3-dioxane-5-yl)-amine (4) (79 mg, 0.322 mmol) in pyridine (2.5 ml) and dichloromethane (5 ml). The mixture was stirred for 5 hours at 60° C. before being diluted with ethyl acetate (80 ml) and successively washed with saturated sodium bicarbonate solution (2×25 ml) and brine (25 ml). Drying over magnesium sulfate, concentration and purification by flash chromatography (hexane/ethyl acetate, 1.5:1) gave bis-N-(2,2-dimethyl-1,3-dioxane-5-yl)-p-nitrobenzamide (10) (91 mg, 72%) as colourless crystals; mp.: 211° C. (needles, from hexane/acetone); m/z (CI, NH3) 337 (M+H+-acetone, 100%).

Workup

  1. washsuccessively washed with saturated sodium bicarbonate solution (2×25 ml) and brine (25 ml)
  2. dry with materialDrying over magnesium sulfate, concentration and purification by flash chromatography (hexane/ethyl acetate, 1.5:1)

Sources & evidence

ORD record
ord-51bc665342304546b8a60aad767be83c
Source dataset
uspto-grants-2005_07
Patent number
US06916948B2

Reaction notes

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