Triethylamine → Benzenesulfonamide

HRID 1657619노트

반응식

HRID 1657619 반응식
Cl.NCC[C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.CC1N=CSC=1C(Cl)=O>Cl.O1CCCC1>[C:8]1([S:11]([NH2:14])(=[O:13])=[O:12])[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 123345284-(2-Aminoethyl)benzenesulfonamide hydrochlorideHCID 124702104-Methyl-1,3-thiazole-5-carbonyl chloride

생성물 1

HCID 7370Benzenesulfonamide

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 1.18 g. (0.005 mole) of 4-(2-aminoethyl)-benzenesulfonamide hydrochloride [E. Miller et al., Journal of the American Chemical Society, Vol. 62, p. 2099 (1940)] and 1.4 ml. (0.010 mole) of triethylamine in 15 ml. of dry tetrahydrofuran, there was added 805 mg. (0.005 mole) of 4-methyl-5-thiazolecarboxylic acid chloride dissolved in 15 ml. of tetrahydrofuran. The addition caused a slight exothermic reaction to occur, after which the reaction mixture was allowed to stand at ambient temperatures for a period of approximately 16 hours with constant agitation being maintained throughout the entire step. At this point, the spent mixture was poured into 50 ml. of ice water and subsequently acidified with a few drops of 3N aqueous hydrochloric acid. The resulting cream-colored precipitate was then recovered by means of suction filtration, washed well with cold water and thereafter crystallized from acetonitrile (after treatment with activated carbon) to yield 1.8 g (73%) of pure 4-[2-methyl-5-thiazolecarboxamido)ethyl]benzenesulfonamide, m.p. 182°-183°C.

후처리

  1. additionTo a mixture of 1.18 g
  2. additionThe addition
  3. customa slight exothermic reaction
  4. temperaturebeing maintained throughout the entire step
  5. additionAt this point, the spent mixture was poured into 50 ml
  6. filtrationThe resulting cream-colored precipitate was then recovered by means of suction filtration
  7. washwashed well with cold water
  8. customcrystallized from acetonitrile (after treatment with activated carbon)

출처 및 근거

ORD 기록
ord-1d79dd9c76fe4e71b0e669f3537e9852
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03961067

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