Tetrahydrofuran → 1H-Benzo[d][1,2,3]triazol-1-yl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate

HRID 1269381Notes

Reaction equation

HRID 1269381 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)[CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].O1CCCC1.O[N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[N:34]1.Cl.C(N=C=NCCCN(C)C)C>O.C(OCC)(=O)C.CN(C)C=O>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][N:33]4[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=5[N:35]=[N:34]4)=[O:23])=[CH:25][CH:26]=3)[CH:14]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99752244-(5-(4-(Pentyloxy)phenyl)-3-isoxazolyl)benzoic acid

Product 1

HCID 105282731H-Benzo[d][1,2,3]triazol-1-yl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoateYield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoic acid (14.7 kg) obtained in Example 3, tetrahydrofuran (147 L), dimethylformamide (118 L) and 1-hydroxybenzotriazole (7.9 kg) were added at 20–25° C. to a 1500-L glass-lined vessel. And then, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (13.6 kg) was added and stirred for 3 hours at this temperature. The reaction mixture was cooled to below 10° C., and then ethyl acetate (480 L) and water (120 L) were added dropwise at below 25° C. After cooling to 2–7° C., the slurry was stirred for 1 hour at this temperature. The product was collected on a stainless centrifuge and washed with acetonitrile (74 L). The damp solid was dried in a stainless vacuum dryer under vacuum to give 1-[4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoyloxy]-1H-1,2,3-benzotriazole (18.6 kg).

Workup

  1. temperatureThe reaction mixture was cooled to below 10° C.
  2. temperatureAfter cooling to 2–7° C.
  3. stirringthe slurry was stirred for 1 hour at this temperature
  4. customThe product was collected on a stainless centrifuge
  5. washwashed with acetonitrile (74 L)
  6. customThe damp solid was dried in a stainless vacuum dryer under vacuum

Sources & evidence

ORD record
ord-b24e3c6090694a14aa5ac35e6dd1ea7e
Source dataset
uspto-grants-2007_04
Patent number
US07199248B2

Reaction notes

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