1,2-Diaminocyclohexane → (S)-3-(1H-benzo[d]imidazol-5-yl)-4-isopropyloxazolidin-2-one

HRID 452091Notes

Reaction equation

HRID 452091 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)([CH3:3])[CH3:2].I[C:11]1[CH:12]=[C:13]([NH2:18])[C:14]([NH2:17])=[CH:15][CH:16]=1.[F-].[Cs+].[CH:21]1(N)CCCCC1N.C(OCC)(OCC)OCC>[Cu]I>[NH:18]1[C:13]2[CH:12]=[CH:11][C:16]([N:5]3[C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][O:7][C:6]3=[O:9])=[CH:15][C:14]=2[N:17]=[CH:21]1

Participants

7

Reactant 5

HCID 46101,2-DiaminocyclohexaneHCID 25953Cesium fluorideHCID 31214Ethyl orthoformateHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 112070494-Iodobenzene-1,2-diamine

Product 1

HCID 178448157(S)-3-(1H-benzo[d]imidazol-5-yl)-4-isopropyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

The compound was synthesized starting from (S)-4-isopropyloxazolidin-2-one (0.065 g, 0.5 mmol), 4-iodobenzene-1,2-diamine (0.117 g, 0.5 mmol), copper(I) iodide (0.010 g, 0.05 mmol), cesium fluoride (0.276 g, 1 mmol), cyclohexane-1,2-diamine (0.006 mL, 0.05 mmol), triethyl orthoformate (3 mL) as described in method 5 step D.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-1d73ca016b714e09b3b2d5513c4ba371
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

Loading…