Sodium Iodide → HCID 178464468, compound

HRID 25574

Reaction equation

HRID 25574 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:23])[N:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][S:19][CH2:20][CH2:21]Cl)[CH2:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[Na+].[I-].[CH2:26]([NH:28][CH2:29][CH2:30][OH:31])[CH3:27]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:23])[N:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][S:19][CH2:20][CH2:21][N:28]([CH2:26][CH3:27])[CH2:29][CH2:30][OH:31])[CH2:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80722-(Ethylamino)ethanol2×HCID 178485968HCID 178485968, compound

Product 1

HCID 178464468HCID 178464468, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 94 mg (0.25 mmol) of trans-[4-(2-Chloro-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester in 1 ml DMA was treated with a catalytic amount of NaI and with 0.05 ml (0.5 mmol) of 2-ethylaminoethanol and stirred at RT for 16 h. The reaction mixture was stirred for 1 week, adding every day twice 0.05 ml (0.5 mmol) of 2-ethylaminoethanol. The solution was concentrated and the residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to yield after flash column chromatography on silica gel (CH2Cl2/MeOH 95:5) 40 mg (39%) of trans-(4-{2-[Ethyl-(2-hydroxy-ethyl)-amino]-ethylsulfanylmethyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, MS: 429 (MH+, 1Cl).

Workup

  1. stirringThe reaction mixture was stirred for 1 week
  2. concentrationThe solution was concentrated
  3. extractionthe residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×)
  4. washThe organic phases were washed with aqueous 10% NaCl solution
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-6de4b3c8ae5d4f64911ead0ad5a09961
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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