Triethylamine → HCID 9953707, compound

HRID 1018469Notes

Reaction equation

HRID 1018469 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl.[CH3:23][CH:24]1[CH:29]=[C:28]([CH3:30])[CH:27]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[O:26][NH:25]1>ClCCl>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([N:25]2[CH:24]([CH3:23])[CH:29]=[C:28]([CH3:30])[CH:27]([C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[O:26]2)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 18401525HCID 18401525, compound

Product 1

HCID 9953707HCID 9953707, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 4-N-acetylsulphanilyl chloride (2.7 g, 11.55 mmol) and triethylamine (1.95 g, 19.25 mmol) in dichloromethane (50 ml) was added portionwise solid 3,6-dihydro-3,5-dimethyl-6-(4-methoxyphenyl)-2H-1,2-oxazine hydrochloride (1.97 g, 7.70 mmol). The resulting solution was stirred at room temperature for 5 h then washed with water three times, aqueous sodium hydroxide (2M), water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated, the resulting foam was purified on flash silica eluting with ethylacetate-hexane (3:2) to give 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-methoxyphenyl)-2H-1,2-oxazine as a white foam. 1H NMR (CDCl3) δ 1.39(3H,s), 1.41(3H, d), 2.20(3H, s), 3.79(3H, s), 4.45(1H, m), 5.19(1H, s), 5.68(1H, d), 6.80(2H, d), 7.13(2H, d), 7.57(1H, bs), 7.59(2H, d), 7.80(2H, d).

Workup

  1. washthen washed with water three times, aqueous sodium hydroxide (2M), water and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customthe resulting foam was purified on flash silica eluting with ethylacetate-hexane (3:2)

Sources & evidence

ORD record
ord-06e647e335804ae781fc6380e814ac72
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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