Bis(2-Methoxyethyl)amine → HCID 178495923, compound

HRID 2405687Notes

Reaction equation

HRID 2405687 reaction equation
[Br-].[CH3:2][C:3]1[C:16]2[NH2+:15][C:14]3[C:9](=[CH:10][C:11]([Br:17])=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=[C:5](Br)[CH:4]=1.[CH3:19][O:20][CH2:21][CH2:22][NH:23][CH2:24][CH2:25][O:26][CH3:27]>C(Cl)(Cl)Cl>[Br-:17].[CH3:19][O:20][CH2:21][CH2:22][N:23]([CH2:24][CH2:25][O:26][CH3:27])[C:5]1[CH:4]=[C:3]([CH3:2])[C:16]2[C:7]([CH:6]=1)=[S+:8][C:9]1[C:14](=[CH:13][CH:12]=[C:11]([N:23]([CH2:24][CH2:25][O:26][CH3:27])[CH2:22][CH2:21][O:20][CH3:19])[CH:10]=1)[N:15]=2

Participants

4

Reactant 2

HCID 2383Bis(2-Methoxyethyl)amineHCID 67464414HCID 67464414, compound

Product 1

HCID 178495923HCID 178495923, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-methyl-3,7-dibromophenothiazinium bromide (315 mg, 0.7 mmol) in chloroform (15 mL) kept under argon, bis(2-methoxyethyl)amine (0.52 mL, 3.5 mmol) was added (30 min) with vigorous stirring. The mixture was stirred for 3 h and after that extracted once with aqueous HBr (30 mL, 1% v/v) and then twice with water. The organic layer was dried (Na2SO4), concentrated and dried under vacuum (93 mg, 24% yield). The desired final product was purified by flash chromatography.

Workup

  1. extractionafter that extracted once with aqueous HBr (30 mL, 1% v/v) and then twice with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customdried under vacuum (93 mg, 24% yield)
  5. customThe desired final product was purified by flash chromatography

Sources & evidence

ORD record
ord-1413b63e806e4b408972ce4e03ded7f4
Source dataset
uspto-grants-2014_08
Patent number
US08809317B2

Reaction notes

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