Dimethylcarbamoyl Chloride → HCID 22387277, compound

HRID 1072568Notes

Reaction equation

HRID 1072568 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:11][N:12]1[C:20]2[C:15](=[C:16]([OH:21])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[C:22]([O:24][CH3:25])=[O:23].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:11][N:12]1[C:20]2[C:15](=[C:16]([O:21][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 22310990HCID 22310990, compound

Product 1

HCID 22387277HCID 22387277, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dimethylcarbamyl chloride (83 mg) was added to a stirred solution of methyl N-(3,4-dichlorobenzyl)-4-hydroxyindole-2-carboxylate (150 mg), triethylamine (65 mg) and DMAP (5 mg) in dichloromethane. The reaction was stirred for 16 hours at room temperature under an atmosphere of nitrogen. The reaction was washed with hydrochloric acie (2M, 70 ml), saturated aqueous sodium hydrogencarbonate solution, water and saturated sodium chloride solution. Combined organic extracts were dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using 60% ethyl acetate:iso-hexane as eluent to give the product as a colourless gum (132 mg,74%); NMR d (CD3SOCD3) 2.94 (s, 3H), 3.12 (s, 3H), 3.81 (s, 3H), 5.82 (s, 2H), 6.91 (m, 2H), 7.21 (s, 1H), 7.27-7.36 (m, 2H), 7.46 (d, 1H), 7.52 (d, 1H); M/z (+) 421 (MH+).

Workup

  1. washThe reaction was washed with hydrochloric acie (2M, 70 ml), saturated aqueous sodium hydrogencarbonate solution, water and saturated sodium chloride solution
  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-b49c6cb5c9b743dcbba20e89c6dd96c0
Source dataset
uspto-grants-2005_06
Patent number
US06911465B1

Reaction notes

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