Acetic Acid → HCID 67037685, compound

HRID 604936Notes

Reaction equation

HRID 604936 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(O)(=O)C.[Cl:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30][Cl:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.O>[Cl:25][CH2:26][CH2:27][N:28]([CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][C:9]2[CH:19]=[CH:20][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][CH:8]=2)=[CH:12][CH:13]=1)[CH2:29][CH2:30][Cl:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9533Bis(2-chloroethyl)amineHCID 5049666Sodium triacetoxyborohydrideHCID 22135779HCID 22135779, compound

Product 1

HCID 67037685HCID 67037685, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methylsulfonylaminophenoxy)benzaldehyde (1.27 g) in dimethylformamide (5 mL)/acetic acid (0.5 mL) was added N,N-bis(2-chloroethyl)amine (856 mg) and the solution was stirred at room temperature for 10 minutes. Sodium triacetoxyborohydride (31.39 g) was added to the solution, which was stirred at room temperature overnight. Water was added to the reaction mixture, which was extracted with ethyl acetate three times. The extract was washed with brine (30 mL), dried over anhydrous sodium sulfate and concentrated. The obtained residue purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give the title compound (790 mg) having the following physical data.

Workup

  1. stirringwas stirred at room temperature overnight
  2. extractionwas extracted with ethyl acetate three times
  3. washThe extract was washed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-71839ced3d874f7581509adb84841bcf
Source dataset
uspto-grants-2011_03
Patent number
US07910741B2

Reaction notes

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