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

HRID 706303Notes

Reaction equation

HRID 706303 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C:5](=[O:7])[NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[C:16]1[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=1.[C:24](=O)([O-])[O-].[K+].[K+].C1(N)CCCCC1N.Cl>[Cu]I.C(O)=O>[NH:23]1[C:18]2[CH:17]=[C:16]([N:4]3[C@@H:3]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:2]([CH3:14])([CH3:1])[O:6][C:5]3=[O:7])[CH:21]=[CH:20][C:19]=2[N:22]=[CH:24]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 46101,2-DiaminocyclohexaneHCID 11430Potassium CarbonateHCID 3235934-Bromobenzene-1,2-diamineHCID 2733820(S)-(+)-5,5-Dimethyl-4-phenyl-2-oxazolidinone

Product 1

HCID 51029940(S)-3-(1H-benzo[d]imidazol-6-yl)-5,5-dimethyl-4-phenyloxazolidin-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 (S)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.25 g, 1.31 mmol), 4-bromobenzene-1,2-diamine (0.245 g, 1.31 mmol), copper(I) iodide (0.025 g, 0.13 mmol), potassium carbonate (0.362 g, 2.62 mmol), cyclohexane-1,2-diamine (0.015 mL, 0.13 mmol), 5N HCl (6.5 mL), formic acid (0.648 mL) as described in method 5 step D

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-ae307887cb5a4d2081f68719be93d9df
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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