Dichloromethane methanol → HCID 57527175, compound

HRID 1671789Notes

Reaction equation

HRID 1671789 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:14]([C:16]2[CH:28]=[CH:27][C:19]3[N:20]=[C:21]([NH:23][CH:24]([CH3:26])[CH3:25])[S:22][C:18]=3[CH:17]=2)[OH:15])SCCCS1.C[OH:30].C(Cl)Cl>C(#N)C.O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:30])[CH:14]([OH:15])[C:16]1[CH:28]=[CH:27][C:19]2[N:20]=[C:21]([NH:23][CH:24]([CH3:26])[CH3:25])[S:22][C:18]=2[CH:17]=1

Participants

6

Reactant 2

HCID 21226129Dichloromethane methanolHCID 57527217HCID 57527217, compound

Product 1

HCID 57527175HCID 57527175, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-(2-fluorophenyl)-1,3-dithian-2-yl)(2-(isopropylamino)benzo[d]thiazol-6-yl)methanol (0.540 g, 1.24 mmol) in acetonitrile (8 mL) and water (1.3 mL) was added a solution bis(trifluoroacetoxy)idobenzene (0.800 g, 1.86 mmol) in acetonitrile (4 mL) at rt over 5 min. The mixture was stirred at rt for 1 hr before it was diluted with AcOEt (100 mL), washed successively with saturated NaHCO3 solution and brine, and dried over anhydrous MgSO4. The title compound (87.0 mg, 20% yield) was isolated as a light yellow waxy material by silica gel chromatography (3% MeOH/CH2Cl2).

Workup

  1. washwashed successively with saturated NaHCO3 solution and brine
  2. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-f0bb33fef7fd4964aa8b062768ed2c22
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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