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

HRID 452090
Notes
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Reaction equation

HRID 452090 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:14]1[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=1.[C:22](=O)([O-])[O-].[K+].[K+].C1(N)CCCCC1N.Cl>[Cu]I.C(O)=O>[NH:21]1[C:16]2[CH:15]=[C:14]([N:8]3[C@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:11][O:10][C:9]3=[O:12])[CH:19]=[CH:18][C:17]=2[N:20]=[CH:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 46101,2-DiaminocyclohexaneHCID 11430Potassium CarbonateHCID 3235934-Bromobenzene-1,2-diamineHCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 58229172(R)-3-(1H-benzo[d]imidazol-6-yl)-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 (R)-4-phenyloxazolidin-2-one (1 equiv., 0.163 g, 1 mmol), 4-bromobenzene-1,2-diamine (1 equiv., 0.187 g, 1 mmol), copper(I) iodide (0.1 equiv., 0.019 g, 0.1 mmol), potassium carbonate (2 equiv., 0.276 g, 2 mmol), cyclohexane-1,2-diamine (0.1 equiv., 0.012 mL, 0.1 mmol), 5N HCl (3.4 mL), formic acid (0.343 mL) as described in method 5 step D.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-982164221e9645828fc8576559b0bf5c
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486940B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes