Sodium Hydroxide → 1-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]-2-aminoethane

HRID 1757479Notes

Reaction equation

HRID 1757479 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[O:17][CH2:18][C:19]([NH2:21])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC(S(NCCC2C=C(C=CC=2)OCCCC(O)=O)(=O)=O)=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[BH4-].[Na+].[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[O:17][CH2:18][CH2:19][NH2:21])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 193881183-[2-(4-Chlorobenzenesulphonamido)-ethyl]-phenoxyacetic acid amideHCID 193881404-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]butyric acid

Product 1

HCID 193880601-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]-2-aminoethane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 21.6 g (58.6 mmol) 3-[2-(4-chlorophenylsulphonylamino)-ethyl]-phenoxyacetamide and 175 ml dimethoxyethane one adds portionwise at 15°-20° C. 31.3 g (0.234 mol) anhydrous aluminium chloride and allows to stir further for 30min. One then adds 8.85 g (0.234 mol) NaBH4 portionwise thereto at 15°-20° C. within 1/2 hr. After 3 hrs. stirring while cooling, 130 ml ice-water are carefully added dropwise thereto, whereby the internal temperature is not to exceed 25° C. While cooling withice, one brings the pH value to 8.5 by addition of conc. NaOH, adds 75 ml ethyl acetate thereto and filters. The precipitate is after-washed with ethyl acetate. After separation of the phases, the aqueous phase is also extracted with ethyl acetate. The organic extracts are dried, concentratedto about 80 ml and mixed with 20 ml HCl-containing ether. After cooling, one filters off with suction and then washes with ethyl acetate. Yield 16.7 g (73% of theory) of hydrochloride with the m.p. 187°-190° C.

Workup

  1. waitat 15°-20° C. within 1/2 hr
  2. waitAfter 3 hrs
  3. stirringstirring
  4. temperaturewhile cooling
  5. customto exceed 25° C
  6. temperatureWhile cooling withice, one
  7. washThe precipitate is after-washed with ethyl acetate
  8. customAfter separation of the phases
  9. extractionthe aqueous phase is also extracted with ethyl acetate
  10. customThe organic extracts are dried
  11. additionmixed with 20 ml HCl-
  12. additioncontaining ether
  13. temperatureAfter cooling

Sources & evidence

ORD record
ord-5323c1d6efe14204ae5d46d896783ea1
Source dataset
uspto-grants-1995_08
Patent number
US05446065

Reaction notes

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