Diethanolamine → HCID 10360491, compound

HRID 1899058Notes

Reaction equation

HRID 1899058 reaction equation
Cl[C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.[NH:18]([CH2:22][CH2:23][OH:24])[CH2:19][CH2:20][OH:21]>O1CCOCC1>[OH:21][CH2:20][CH2:19][N:18]([C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1)[CH2:22][CH2:23][OH:24]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 149270775-Chloro-2,4-dinitrobenzenesulfonamide

Product 1

HCID 10360491HCID 10360491, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-chloro-2,4-dinitrobenzenesulfonamide (VIII) [Herbert, R. B. and Hollman, R. G. Tetrahedron, 1965, 21, 663-675] (1.55 g, 5.5 mmol) and diethanolamine (1.16 g, 11 mmol) in dioxan (100 mL) was held at 60° C. for 1.5 h, then adsorbed directly onto silica gel. Excess solvent was evaporated under reduced pressure, and the residue was chromatographed on silica gel, eluting with EtOAc/MeOH (19:1), to give 5-[N,N-bis(2-hydroxyethyl)amino]-2,4-dinitrobenzenesulfonamide (IX) (1.91 g, 99%), mp (EtOAc/petroleum ether) 138°-139° C. 1H NMR ((CD3)2SO) δ 8.53 (s, 1 H, H-3), 7.97 (s, 1 H, H-6), 7.93 (br s, 2 H, SO2NH2), 4.88 (t, J=5.1 Hz, 2 H, OH), 3.65 (dt, J=5.2, 5.1 Hz, 4 H, CH2OH), 3.49 (t, J=5.1 Hz, 4 H, NCH2). 13C NMR δ 146.84 (C-5), 140.53 (C-1), 136.84, 134.39 (C-2,4), 125.70 (C-3), 54.27 (NCH2). Anal. (C10H14N4O8S) C,H,N.

Workup

  1. customExcess solvent was evaporated under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. washeluting with EtOAc/MeOH (19:1)

Sources & evidence

ORD record
ord-978cb9ce0ae4458c9e623e15b148c92d
Source dataset
uspto-grants-1996_11
Patent number
US05571845

Reaction notes

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