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Water → 5-Chloro-3-[2-tritylamino-3-(1-trityl-4-imidazolyl)propoxy]-1,2-benzoisoxazole

HRID 1901641
Notes
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Reaction equation

HRID 1901641 reaction equation
[C:1]([NH:20][CH:21]([CH2:24][C:25]1[N:26]=[CH:27][N:28]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=1)[CH2:22][OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:52]1[C:56]2[CH:57]=[C:58]([Cl:61])[CH:59]=[CH:60][C:55]=2[O:54][N:53]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:61][C:58]1[CH:59]=[CH:60][C:55]2[O:54][N:53]=[C:52]([O:23][CH2:22][CH:21]([NH:20][C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:24][C:25]3[N:26]=[CH:27][N:28]([C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:29]=3)[C:56]=2[CH:57]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 135684483,5-Dichloro-1,2-benzoxazoleHCID 233684162-Tritylamino-3-(1-trityl-4-imidazolyl)-1-propanol

Product 1

HCID 233683685-Chloro-3-[2-tritylamino-3-(1-trityl-4-imidazolyl)propoxy]-1,2-benzoisoxazole

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
3×
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.0 g of 2-tritylamino-3-(1-trityl-4-imidazolyl)-1-propanol in 10 ml of N,N-dimethylformamide is dropwise added to a suspension of 0.14 g of 60% (w/w) sodium hydride in 15 ml of N,N-dimethylformamide at room temperature over 15 minutes, and the temperature is then elevated gradually to 80° C., after which this is added to a solution of 0.6 g of 3,5-dichloro-1,2-benzoisoxazole in 10 ml of N,N-dimethylformamide. They are subjected to reaction at the same temperature for six hours. After cooling, water and ethyl acetate are added and shaken, and the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=3:1], to obtain 1.12 g of colorless, crystalline 5-chloro-3-[2-tritylamino-3-(1-trityl-4-imidazolyl)propoxy]-1,2-benzoisoxazole having a melting point of 113.4°-114.7° C.

Workup

  1. customis then elevated gradually to 80° C.
  2. customThey are subjected to reaction at the same temperature for six hours
  3. temperatureAfter cooling
  4. customthe organic layer is separated
  5. washThe separated organic layer is washed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent is removed by distillation under reduced pressure
  8. customThe residue obtained
  9. customis purified by a column chromatography [eluant:n-hexane:ethyl acetate=3:1]

Sources & evidence

ORD record
ord-bf166d6133e749fdac8664feb9566c8e
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05578627

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes