Diethanolamine → HCID 68702307, compound

HRID 1865802Notes

Reaction equation

HRID 1865802 reaction equation
F[C:2]1[C:3]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[NH:19]([CH2:23][CH2:24][OH:25])[CH2:20][CH2:21][OH:22]>CC(N(C)C)=O.CCOC(C)=O>[OH:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][OH:25])[C:2]1[C:3]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 8113DiethanolamineHCID 68702168HCID 68702168, compound

Product 1

HCID 68702307HCID 68702307, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 4 (1.48 g, 5.34 mmol) and diethanolamine (1.40 g, 13.3 mmol) in DMA (6 mL) was stirred at 30° C. for1 h, and then diluted with EtOAc (60 mL). The solution was washed with brine (2×) and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with EtOAc/MeOH, followed by recrystallization from EtOAc/iPr2O, to give methyl 5-[bis(2-hydroxyethyl)amino]-4-(methylsulfonyl)-2-nitrobenzoate (5) (1.41 g, 73%): mp 99-100° C.; 1H NMR [(CD3)2SO] δ 8.56 (s, 1 H), 7.73 (s, 1 H), 4.62 (t, J=4.9 Hz, 2 H), 3.89 (s, 3 H), 3.59-3.49 (m, 8 H), 3.45 (s, 3 H). Anal. (C13H18N2O8S) C, H, N.

Workup

  1. washThe solution was washed with brine (2×)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with EtOAc/MeOH
  5. customfollowed by recrystallization from EtOAc/iPr2O

Sources & evidence

ORD record
ord-d94ee12da7fe4edf8bc4924d98c37d6c
Source dataset
uspto-grants-2009_12
Patent number
US07629332B2

Reaction notes

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