Diethanolamine → HCID 86601658, compound

HRID 503680Notes

Reaction equation

HRID 503680 reaction equation
Cl[C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:5].[NH:26]([CH2:30][CH2:31][OH:32])[CH2:27][CH2:28][OH:29]>O1CCOCC1.[Cl-].[Na+].O>[OH:29][CH2:28][CH2:27][N:26]([CH2:30][CH2:31][OH:32])[C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:5]

Participants

5

Reactant 2

HCID 8113DiethanolamineHCID 85962066HCID 85962066, compound

Product 1

HCID 86601658HCID 86601658, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Chloro-N-[3-(4-morpholinyl)propyl]-3,5-dinitrobenzamide (12h) (0.5 g, 1.34 mmol) was reacted with diethanolamine (0.5 g) in p-dioxane (10 mL) at room temperature for 3 h. The reaction mixture was poured into brine, extracted with EtOAc (3×70 mL), and the combined organic phases were dried and concentrated under reduced pressure to give crude 2-[bis(2-hydroxyethyl)amino]-N-[3-(4-morpholinyl)propyl]-3,5-dinitrobenzamide. This was dissolved in CH2Cl2 (100 mL), cooled in an ice-bath, and treated with Et3N (1.5 mL) followed by MsCl (0.7 mL) in one portion. After stirring for 10 min, sat. NaHCO3 (100 mL) was added and the mixture was stirred for a further 30 min, then the aqueous phase was extracted with CH2Cl3 (2×70 mL). The combined organic phases were dried and evaporated under reduced pressure. The residue was purified by column chromatography, eluting with EtOAc/MeOH (20:1 to 9:0) to give yield 2-[{2-[(methylsulfonyl)oxy]ethyl}-2-({[3-(4-morpholinyl)propyl]amino}carbonyl)-4,6-dinitroanilino]ethyl methanesulfonate (13h) (0.75 g, 93%) as a foam;

Workup

  1. extractionextracted with EtOAc (3×70 mL)
  2. customthe combined organic phases were dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73e578ccdc654e80925cf8d55fac191f
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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