Water → 4-{2-[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-ethyl}-benzonitrile

HRID 1441696Notes

Reaction equation

HRID 1441696 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[N:17]=2)=O)=[CH:5][CH:4]=1)#[N:2].O>O1CCCC1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[N:17]=[C:13]([NH:12][CH2:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[S:14][CH:15]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 962WaterHCID 591645722-(4-Cyano-phenyl)-N-[4-(4-methoxy-phenyl)-thiazol-2-yl]-acetamide

Product 1

HCID 591646184-{2-[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-ethyl}-benzonitrileYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

610 mg 2-(4-Cyano-phenyl)-N-[4-(4-methoxy-phenyl)-thiazol-2-yl]-acetamide were suspended in 20 ml tetrahydrofuran. 2.1 ml of a one molar solution of borane tetrahydrofuran complex were added at room temperature. The reaction mixture was stirred at room temperature for two hours and then at 50° C. for two hours. The cooled reaction mixture was poured on 50 ml water and extracted five times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4. Then the solvents were removed in vacuo to obtain 600 mg 4-{2-[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-ethyl}-benzonitrile.

Workup

  1. waitat 50° C. for two hours
  2. customThe cooled reaction mixture
  3. extractionextracted five times with portions of 50 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThen the solvents were removed in vacuo

Sources & evidence

ORD record
ord-e41c4c1ce541482ab0b06161dae3f712
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

Loading…