Dimethylformamide → HCID 57317869, compound

HRID 1737288Notes

Reaction equation

HRID 1737288 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:13])[C:10](Cl)=[O:11].[N+:14]([C:17]1[CH:18]=[C:19]([CH:24]([CH:27]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[CH2:28][CH3:29])[CH2:25][CH3:26])[CH:20]=[CH:21][C:22]=1[OH:23])([O-:16])=[O:15].[CH3:37][N:38]([CH3:41])[CH:39]=[O:40]>CN(C)C1C=CN=CC=1.O>[N+:14]([C:17]1[CH:18]=[C:19]([CH:24]([CH:27]([C:30]2[CH:31]=[CH:32][C:33]([O:36][C:39](=[O:40])[N:38]([CH3:41])[CH3:37])=[CH:34][CH:35]=2)[CH2:28][CH3:29])[CH2:25][CH3:26])[CH:20]=[CH:21][C:22]=1[O:23][C:10](=[O:11])[N:9]([CH3:13])[CH3:8])([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 57246321HCID 57246321, compound

Product 1

HCID 57317869HCID 57317869, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (13.8 ml), dimethylcarbamoyl chloride (9 ml) and 4-dimethylaminopyridine (125 mg) were added in that order to a solution of erythro 3-(3-nitro-4-hydroxyphenyl)-4-(4-hydroxyphenyl)hexane (4.21 g) in dry N,N-dimethylformamide (90 ml) at 0-5° C., and the resulting mixture was heated to room temperature and stirred for 2 days. The reaction mixture was diluted with water and extracted twice with a mixed solvent of diethyl ether and ethyl acetate. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain erythro 3-(3-nitro-4-dimethylcarbamoyloxyphenyl)-4-(4-dimethylcarbamoyloxyphenyl)hexane (5.14 g, quantitative yield).

Workup

  1. extractionextracted twice with a mixed solvent of diethyl ether and ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b63904535761458ca0bec6a235a421ac
Source dataset
uspto-grants-1999_10
Patent number
US05962438

Reaction notes

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