Water → methyl 3-[4-(N-Benzoxazol-2-yl)aminobutoxy]benzoate

HRID 1594436Notes

Reaction equation

HRID 1594436 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].C(N(CC)C(C)C)(C)C.Cl[C:27]1[O:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.O>O1CCCC1>[O:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 58678502Methyl 3-(4-aminobutoxy)benzoate

Product 1

HCID 58678487methyl 3-[4-(N-Benzoxazol-2-yl)aminobutoxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(4-aminobutoxy)benzoate (4.81 g) was dissolved in 50.0 mL of tetrahydrofuran and N,N-diisopropylethylamine (2.90 g, 22.4 mmol) was added. Under cooling, 2-chlorobenzoxazole (3.44 g, 22.4 mmol) was added dropwise thereto and stirred overnight at room temperature. Following the addition of water, the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine. The organic layer was dried with sodium sulfate and then concentrated under reduced pressure, followed by purification by silica gel column chromatography (hexane:ethyl acetate=4:1) to give a compound of interest (3.22 g, 50.7%).

Workup

  1. temperatureUnder cooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (hexane:ethyl acetate=4:1)
  7. customto give a compound of interest (3.22 g, 50.7%)

Sources & evidence

ORD record
ord-36d2233bb2884eacbc02854ee01ab3d8
Source dataset
uspto-grants-2007_11
Patent number
US07301033B2

Reaction notes

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