Hydrochloric Acid → N-[5-[(HEXADECYLSULFONYL)AMINO]-2-METHOXYPHENYL]-2,2,5-TRIMETHYL-beta-OXO-1,3-DIOXANE-5-PROPANAMIDE

HRID 892405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892405
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([NH:8][C:9](=[O:22])[CH2:10][C:11](=[O:21])[C:12]2([CH3:20])[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]2)[CH:7]=1.CN(C)C1C=CC=CC=1.[CH2:34]([S:50](Cl)(=[O:52])=[O:51])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].Cl>O1CCCC1.O>[CH2:34]([S:50]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([NH:8][C:9](=[O:22])[CH2:10][C:11](=[O:21])[C:12]2([CH3:20])[CH2:17][O:16][C:15]([CH3:18])([CH3:19])[O:14][CH2:13]2)[CH:7]=1)(=[O:52])=[O:51])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 969231-Hexadecanesulfonyl chlorideHCID 53685390N-(5-AMINO-2-METHOXYPHENYL)-2,2,5-TRIMETHYL-beta-OXO-1,3-DIOXANE-5-PROPANAMIDE

Produkt 1

HCID 18417948N-[5-[(HEXADECYLSULFONYL)AMINO]-2-METHOXYPHENYL]-2,2,5-TRIMETHYL-beta-OXO-1,3-DIOXANE-5-PROPANAMIDE

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The amine product of Reaction Example 8, N-(5-amino-2-methoxyphenyl)-2,2,5-trimethyl-β-oxo-1,3-dioxane-5-propanamide, (18.5 parts) and N,N-dimethylaniline (8.5 parts) are combined in tetrahydrofuran (250 parts) and a solution of 1-hexadecylsulfonyl chloride (17.9 parts) dissolved in tetrahydrofuran (25 parts) is added dropwise with stirring, ca. 0.5 hr. The reaction is allowed to stand several hours and subsequently poured into cold water (600 parts) containing concentrated hydrochloric acid (5 parts). The crude product is extracted with ethyl ether and the ethereal layer washed once with sodium bicarbonate solution, once with water, dried over magnesium sulfate, filtered and subsequently flash evaporated in vacuo to give a light tan product in 90% of theoretical yield. Analytical samples are crystallized from ethyl alcohol, m.p. 83-85° C. Proton NMR and combustion analysis are consistent with those values predicted for the desired product. Combustion Analysis for C33H56N2O6S--Calculated: C, 65.1%; H, 9.3%; N, 4.6%; S, 5.3%. Found: C, 65.6%; H, 9.1; N, 4.4%; S, 5.0%.

Aufarbeitung

  1. additionis added dropwise
  2. waitto stand several hours
  3. extractionThe crude product is extracted with ethyl ether
  4. washthe ethereal layer washed once with sodium bicarbonate solution, once with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsubsequently flash evaporated in vacuo
  8. customto give a light tan product in 90% of theoretical yield
  9. customAnalytical samples are crystallized from ethyl alcohol, m.p. 83-85° C

Quellen und Nachweise

ORD-Eintrag
ord-29dc52415cab4d47b378a735a41322a6
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118599

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