Hydrochloric Acid → HCID 87461051, compound

HRID 503674Notes

Reaction equation

HRID 503674 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:9]1[C:10]([N+:21]([O-:23])=[O:22])=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)(=[O:4])=[O:3].CN(C=O)C.[NH2:36][CH2:37][CH2:38][CH2:39][OH:40].Cl>O=S(Cl)Cl>[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:9]1[CH:17]=[C:13]([C:14]([NH:36][CH2:37][CH2:38][CH2:39][OH:40])=[O:16])[C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 90863-Amino-1-propanolHCID 16115119HCID 16115119, compound

Product 1

HCID 87461051HCID 87461051, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

5-(Bis {2-[(methylsulfonyl)oxy]ethyl}amino)-2,4-dinitrobenzoic acid (8) was heated under reflux in excess SOCl2 (60 mL) and catalytic DMF for 1 h. Evaporation under reduced pressure, followed by azeotroping in benzene, gave the crude acid chloride. This was dissolved in dry Me2CO and treated at 0° C. with 3-amino-1-propanol at 0° C. for 5 min. The mixture was acidified to pH 2-3 with 0.2 N HCl, concentrated to half volume, and then solid NaBr was added, followed by extraction with EtOAc (2×). Evaporation, and chromatography of the residue on silica gel, eluting with EtOAc/MeOH (9:1), gave 2-(5-{[(3-hydroxypropyl)amino]carbonyl}{2-[(methylsulfonyl)oxy]ethyl}-2,4-dinitroanilino)ethyl methanesulfonate (9b) (68%) as a yellow gum;

Workup

  1. customEvaporation under reduced pressure
  2. customby azeotroping in benzene
  3. customgave the crude acid chloride
  4. dissolutionThis was dissolved in dry Me2CO
  5. concentrationconcentrated to half volume
  6. additionsolid NaBr was added
  7. extractionfollowed by extraction with EtOAc (2×)
  8. customEvaporation, and chromatography of the residue on silica gel
  9. washeluting with EtOAc/MeOH (9:1)

Sources & evidence

ORD record
ord-5f3876fac7dd4f908090d59282d55f68
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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