Water → 5-Chloro-3-[2-(2-methyl-1,3-thiazol-5-yl)-2-tritylaminoethoxy]-1,2-benzoisoxazole

HRID 1901628Notes

Reaction equation

HRID 1901628 reaction equation
[H-].[Na+].[CH3:3][C:4]1[S:5][C:6]([CH:9]([NH:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][OH:11])=[CH:7][N:8]=1.Cl[C:33]1[C:37]2[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:36]=2[O:35][N:34]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]2[O:35][N:34]=[C:33]([O:11][CH2:10][CH:9]([C:6]3[S:5][C:4]([CH3:3])=[N:8][CH:7]=3)[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:37]=2[CH:38]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 135684483,5-Dichloro-1,2-benzoxazoleHCID 233683832-(2-Methyl-1,3-thiazol-5-yl)-2-tritylaminoethanol

Product 1

HCID 233685165-Chloro-3-[2-(2-methyl-1,3-thiazol-5-yl)-2-tritylaminoethoxy]-1,2-benzoisoxazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.24 g of 60% sodium hydride in 10 ml of N,N-dimethylformamide are dropwise added 2.0 g of 2-(2-methyl-1,3-thiazol-5-yl)-2-tritylaminoethanol, a solution of 10 ml of N,N-dimethylformamide at room temperature, and the temperature is gradually elevated to 80° C. after which 1.03 g of 3,5-dichloro-1,2-benzoisoxazole is added. They are subjected to reaction at the same temperature for one hour. After cooling, water and ethyl acetate are added, and the crystals precipitated are collected by filtration. The organic layer of the filtrate is separated, washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The crystals obtained are combined with the crystals previously collected by filtration to obtain 1.81 g of colorless, crystalline 5-chloro-3-[2-(2-methyl-1,3-thiazol-5-yl)-2-tritylaminoethoxy]-1,2-benzoisoxazole.

Workup

  1. customat room temperature
  2. customis gradually elevated to 80° C.
  3. additionis added
  4. customThey are subjected to reaction at the same temperature for one hour
  5. temperatureAfter cooling
  6. customthe crystals precipitated
  7. filtrationare collected by filtration
  8. customThe organic layer of the filtrate is separated
  9. washwashed with a saturated saline solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customafter which the solvent is removed by distillation under reduced pressure
  12. customThe crystals obtained
  13. filtrationpreviously collected by filtration

Sources & evidence

ORD record
ord-33e1e6c10777481e82e0de4e9c8b15a6
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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