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

HRID 892405노트

반응식

HRID 892405 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-29dc52415cab4d47b378a735a41322a6
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05118599

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