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Hydrochloric Acid → 5-Chloro-3-(2-tritylamino-3-hydroxypropoxy)-1,2-benzoisoxazole

HRID 1901600
Notes
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Reaction equation

HRID 1901600 reaction equation
[C:1](Cl)([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.[NH2:21][CH:22]([CH2:35][OH:36])[CH2:23][O:24][C:25]1[C:29]2[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=2[O:27][N:26]=1.C(N(CC)CC)C.Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]2[O:27][N:26]=[C:25]([O:24][CH2:23][CH:22]([NH:21][C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:35][OH:36])[C:29]=2[CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 153825803-(2-Amino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 233684925-Chloro-3-(2-tritylamino-3-hydroxypropoxy)-1,2-benzoisoxazole

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.58 g of trityl chloride in 6 ml of N,N-dimethylformamide is added to a solution of 4.85 g of 3-(2-amino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole and 2.02 g of triethylamine in 12 ml of N,N-dimethylformamide at -40° to -30° C., and they are subjected to reaction at the same temperature for 30 minutes. Subsequently, ice water and ethyl acetate are added to the reaction mixture and the pH is adjusted to 2 with 2N hydrochloric acid. The organic layer is separated, and 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 crystallized from n-hexane and the crystals are collected by filtration, to obtain 7.28 g of colorless, crystalline 5-chloro-3-(2-tritylamino-3-hydroxypropoxy)-1,2-benzoisoxazole having a melting point of 142°-144° C.

Workup

  1. customthey are subjected to reaction at the same temperature for 30 minutes
  2. customThe organic layer is separated
  3. washthe separated organic layer is washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent is removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customis crystallized from n-hexane
  8. filtrationthe crystals are collected by filtration

Sources & evidence

ORD record
ord-ca787c46f3524ff7b57cd5a82caa3689
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