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

HRID 892405Notes

Reaction equation

HRID 892405 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-29dc52415cab4d47b378a735a41322a6
Source dataset
uspto-grants-1992_06
Patent number
US05118599

Reaction notes

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