Ethanolamine → 2-Amino-5-(4-[2-hydroxyethyl]aminophenylsulfonyloxy)nitrobenzene

HRID 1823761Notes

Reaction equation

HRID 1823761 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[CH2:22]([CH2:24][NH2:25])[OH:23]>CCOCCO.Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:25][CH2:24][CH2:22][OH:23])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 120188434-Amino-3-nitrophenyl 4-fluorobenzenesulfonate

Product 1

HCID 120188442-Amino-5-(4-[2-hydroxyethyl]aminophenylsulfonyloxy)nitrobenzene

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

15.6 g of 2-amino-5-(4-fluorophenylsulfonyloxy)nitrobenzene were combined with 25 ml ethanolamine in 100 ml ethyl glycol in a round bottom flask. The reaction mixture was heated to reflux for 90 min and then cooled on ice. Reaction mixture was then diluted with 250 ml of 2N aqueous HCl, the compound precipitated and was filtered off with suction. The preciptate was the washed with water and dried, yielding 15.5 g of 2-amino-5-(4-[2-hydroxyethyl]aminophenylsulfonyloxy)nitrobenzene (melting point 180° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 90 min
  3. temperaturecooled on ice
  4. customReaction mixture
  5. customthe compound precipitated
  6. filtrationwas filtered off with suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-04eeb12c40554426b59a777a8d6f45d5
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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