Dimethylformamide → HCID 22997277, compound

HRID 1166054Notes

Reaction equation

HRID 1166054 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15]O)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].CN(C)C=O.S(Cl)([Cl:33])=O>ClCCl>[Cl:33][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:6]2[CH2:5][C:4]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22997275HCID 22997275, compound

Product 1

HCID 22997277HCID 22997277, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl N-(3,4-dichlorobenzyl)-4-hydroxymethylindole-2-carboxylate (0.89 g), dimethylformamide (0.5 ml) and thionyl chloride (189 μl) in dichloromethane (40 ml) were stirred at ambient temperature overnight and the resulting precipitate as filtered and dried in vacuo to give the product as a white solid (0.62 g, 67%); NMR δ(CD3SOCD3) 1.30 (t, 3H), 4.30 (q, 2H), 5.10 (s, 2H), 5.85 (s, 2H), 6.90 (m, 1H), 7.30 (m, 3H) 7.55 (m, 3H), M/z (+) 396.2 (MH+).

Workup

  1. filtrationthe resulting precipitate as filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-59b062a9b2fc4b529abe0b9a9692b5c9
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

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