Chlorosuccinimide → HCID 68486489, compound

HRID 1874945Notes

Reaction equation

HRID 1874945 reaction equation
C1C(=O)N(Cl)C(=O)C1.C[S:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17]2>CN(C=O)C>[S:10]1[C:15]2=[C:16]3[C:20](=[CH:21][CH:22]=[C:14]2[O:13][CH2:12][CH2:11]1)[NH:19][C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17]3

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68485442HCID 68485442, compound

Product 1

HCID 68486489HCID 68486489, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NCS (0.048 g, 0.358 mmol) was added to a DMF (2 mL) solution of ethyl 5-{[2-(methylthio)ethyl]oxy}-1H-indole-2-carboxylate (0.100 g, 0.358 mmol) and the reaction mixture stirred over the weekend at room temperature. The reaction mixture was partitioned between water and EtOAc and the organic layer was separated. The organic layer was dried over MgSO4, filtered and evaporated onto silica. Purification was accomplished by silica gel column chromatography (0-50% EtOAc/hexanes) to afford the title compound (0.067 g, 71%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.38 (br. s., 1H), 7.11 (s, 1H), 7.04 (d, 1H), 6.85 (d, 1H), 4.35-4.47 (m, 4 H), 3.16-3.24 (m, 2H), 1.41 (t, 3H). LCMS: m/z=264 (M+1).

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated onto silica
  6. customPurification

Sources & evidence

ORD record
ord-fc494115d19c45c6bbfc8d1b80a40e46
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…