HCID 22048460, compound → HCID 22048470, compound

HRID 1830804Notes

Reaction equation

HRID 1830804 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([C:19]4[S:20][CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[N:23]=4)=[O:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1>O.C1COCC1>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=2)=[O:18])=[CH:13][C:12]=1[C:8](=[O:9])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 1

HCID 22048460HCID 22048460, compound

Product 1

HCID 22048470HCID 22048470, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

TiCl3 15% in water (300 ml) was added slowly at room temperature to a mixture of intermediate (15) (0.0656 mol) in THF (500 ml). The mixture was stirred at room temperature overnight, then poured out into ice water, extracted with DCM and washed with K2CO3 10%. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 25.5 g (92.7%) of [4-amino-3-(3-chlorobenzoyl)phenyl](4-phenyl-2-thiazolyl)-methanone (intermediate 16).

Workup

  1. extractionextracted with DCM
  2. washwashed with K2CO3 10%
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-11dc14bbbb2246359f1d675dddbe903d
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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