Hydrochloric Acid → (4S,5R)-3-(1H-benzo[d]imidazol-6-yl)-4,5-diphenyloxazolidin-2-one

HRID 452093

Reaction equation

HRID 452093 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:20]1[CH:21]=[C:22]([NH2:27])[C:23]([NH2:26])=[CH:24][CH:25]=1.[C:28](=O)([O-])[O-].[K+].[K+].C1(N)CCCCC1N.Cl>[Cu]I.C(O)=O>[NH:27]1[C:22]2[CH:21]=[C:20]([N:8]3[C@@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C@@H:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[O:10][C:9]3=[O:18])[CH:25]=[CH:24][C:23]=2[N:26]=[CH:28]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 46101,2-DiaminocyclohexaneHCID 11430Potassium CarbonateHCID 3235934-Bromobenzene-1,2-diamineHCID 9859564(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone

Product 1

HCID 58229203(4S,5R)-3-(1H-benzo[d]imidazol-6-yl)-4,5-diphenyloxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 284Formic AcidSolvent

Procedure

The compound was synthesized starting from (4S,5R)-4,5-diphenyloxazolidin-2-one (0.479 g, 2 mmol), 4-bromobenzene-1,2-diamine (0.374 g, 2 mmol), copper(I) iodide (0.038 g, 0.2 mmol), potassium carbonate (0.553 g, 4 mmol), cyclohexane-1,2-diamine (0.024 mL, 0.2 mmol), 5N HCl (5.8 mL), formic acid (0.582 mL) as described in method 5 step D

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-2dd6f40eb9a14500807db04edfdf42df
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Linked notes

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