Ammonia → 4-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]-butyramide

HRID 1757477Notes

Reaction equation

HRID 1757477 reaction equation
C([N:3](CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][CH2:20][C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[O:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(OC(Cl)=O)C.Cl.C(N(CC)CC)C.N>C1COCC1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][CH2:20][C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[O:24][CH2:25][CH2:26][CH2:27][C:28]([NH2:3])=[O:29])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11130Triethylamine hydrochlorideHCID 193881404-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]butyric acid

Product 1

HCID 193880974-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]-butyramide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution cooled to -10° C. of 100 ml abs. THF, 4.32 g (43 mmol)triethylamine and 14.4 g (36 mmol) 4-[3-[2-(4-chlorophenylsulphonylamino)-ethyl]-phenoxy]butyric acid one slowly adds dropwise a mixture of 4.02 g (37 mmol) chloroformic acid ethylester and 30 ml abs. THF. One allows to come to room temperature, stirs a further 30 min and filters off with suction the precipitated triethylaminehydrochloride. The filtrate is then gassed with ammonia with ice cooling. It is then stirred for 6 hrs. at room temperature, evaporated and mixed with 2N HCl. One adds ethyl acetate thereto, mixes up very vigorously and separates the phases. The ethyl acetate phase is shaken out twice with bicarbonate solution and twice with water, then dried with Na2SO4 and evaporated. After recrystallisation from ethyl acetate, one obtains colourless crystals. Yield: 12.8 g (89% of theory); m.p. 110°-112° C.

Workup

  1. customto come to room temperature
  2. customat room temperature, evaporated
  3. additionmixed with 2N HCl
  4. additionOne adds ethyl acetate
  5. stirringThe ethyl acetate phase is shaken out twice with bicarbonate solution and twice with water
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customAfter recrystallisation from ethyl acetate, one
  9. customobtains colourless crystals

Sources & evidence

ORD record
ord-87134b09f2e64856b41b041c1bcd74ee
Source dataset
uspto-grants-1995_08
Patent number
US05446065

Reaction notes

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