Water → HCID 22988707, compound

HRID 987337Notes

Reaction equation

HRID 987337 reaction equation
[CH:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)=[O:2].CN(C(O[N:29]1N=N[C:31]2C=CC=[CH:35][C:30]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N)(C)C.O>CN(C1C=CN=CC=1)C.CN(C=O)C.COCCOC>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:29][CH:30]([CH3:35])[CH3:31])=[O:16])=[CH:17][CH:18]=2)=[CH:19][CH:20]=1)=[O:2]

Participants

8

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22988773HCID 22988773, compound

Product 1

HCID 22988707HCID 22988707, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-[2-(4-Formylphenoxy)ethyl]benzoic acid (8.11 g; 30 mmole), TBTU (10.6 g; 33 mmole) and DMAP (8.1 g; 66 mmole) were dissolved in DMF (85 ml). The reaction mixture was cooled on an ice bath and isopropylamine (12 g; 200 mmole) dissolved in DME (100 ml) was added. The reaction mixture was stirred at room temperature over night. A large amount of water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with potassium hydogen sulfate (0.3 M), water and brine and dried with sodium sulfate. Evaporation gave 8 g (85.6% yield) of 4-[2-(4-formylphenoxy)ethyl]-N-isopropylbenzamide.

Workup

  1. temperatureThe reaction mixture was cooled on an ice bath
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with potassium hydogen sulfate (0.3 M), water and brine
  5. dry with materialdried with sodium sulfate
  6. customEvaporation

Sources & evidence

ORD record
ord-c1143d16f7ba427bbfa3126d42fbf867
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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