3,4-Dichlorobenzyl chloride → HCID 86759581, compound

HRID 2307921Notes

Reaction equation

HRID 2307921 reaction equation
[OH-].[Na+].[CH2:3]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:19]([O:21][CH2:22][CH3:23])=[S:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:28]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:28][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:11]1[C:19]([O:21][CH2:22][CH3:23])=[S:20]

Participants

6

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 87796841HCID 87796841, compound

Product 1

HCID 86759581HCID 86759581, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Powdered sodium hydroxide (3.2 g) was added in a single portion to a vigorously stirred solution of ethyl 3-benzylthioindole-2-carboxylate (2.48 g), 3,4-dichlorobenzyl chloride (1.71 g) and tetra-n-butylammonium hydrogensulphate (0.5 g) in dichloromethane (100 ml). The reaction was stirred for 6 hours then partitioned between 2M HCl and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using iso-hexane:5% ethyl acetate as eluent to give the product as a white crystalline solid (2.26 g, 60%); NMR d (CD3SOCD3) 1.32 (t, 3H), 4.00 (s, 2H), 4.25 (q, 2H), 5.60 (s, 2H), 6.78 (d, 1H), 7.04 (m, 2H), 7.10-7.38 (m, 8H), 7.80 (d, 1H); M/z (+) 470 (M+), 426, 424.

Workup

  1. customthen partitioned between 2M HCl and ethyl acetate
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-dc5eb7574f2a446ca7847190ff85da76
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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