Sulfuric Acid → HCID 20496702, compound

HRID 1074451Notes

Reaction equation

HRID 1074451 reaction equation
S1CCSC1=NC1C=CC(CCCCCCO)=CC=1.C(Cl)(=O)C.[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:45]=[CH:44][C:37]([N:38]=[C:39]2[S:43][CH2:42][CH2:41][S:40]2)=[CH:36][CH:35]=1)(=[O:26])[CH3:25].[S:46](=[O:50])(=[O:49])([OH:48])[OH:47]>C(Cl)Cl.C(OCC)C.C(N(CC)CC)C>[S:46]([OH:50])([OH:49])(=[O:48])=[O:47].[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:35]=[CH:36][C:37]([N:38]=[C:39]2[S:43][CH2:42][CH2:41][S:40]2)=[CH:44][CH:45]=1)(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 13145722HCID 13145722, compoundHCID 13145724HCID 13145724, compound

Product 1

HCID 20496702HCID 20496702, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 1 g of 6-[4-(1,3-dithiolan-2-ylideneamino)phenyl]hexanol and 0.38 g of triethylamine in 20 ml of dried methylene chloride was added dropwise a solution of 0.27 g of acetyl chloride in 10 ml of dried methylene chloride. The resulting solution was stirred at room temperature for 2 hours. It was then washed with 0.1 N hydrochloric acid, twice with water, and once with aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was then removed to give a crude yellow oil which was purified by flash chromatography using 15 cm of silica gel and ethyl acetate/hexane as the eluant. This gave a colorless oil which was 4-(6-acetoxyhexyl)N-(1,3-dithiolan-2-ylidene)aniline. This oil was dissolved in 40 ml of diethyl ether and there was added dropwise a solution of 0.29 g of sulfuric acid and 20 ml of diethyl ether. When the addition was complete, the reaction mixture was placed in a freezer. The precipitate which formed was separated by filtration and recrystallized from acetonitrile/ethyl acetate to give 4-(6-acetoxyhexyl)-N-(1,3-dithiolan-2-ylidene)-aniline dihydrogen sulfate as white needles melting at about 151.5°-153.5° C. The free base of this compound has the following structural formula ##STR6##

Workup

  1. washIt was then washed with 0.1 N hydrochloric acid, twice with water
  2. dry with materialonce with aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate
  3. customThe solvent was then removed
  4. customto give a crude yellow oil which
  5. customwas purified by flash chromatography
  6. customThis gave a colorless oil which
  7. additionWhen the addition
  8. customThe precipitate which formed
  9. customwas separated by filtration
  10. customrecrystallized from acetonitrile/ethyl acetate

Sources & evidence

ORD record
ord-e83e60347e2d45638628f81933c7abb5
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Reaction notes

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