Dimethylformamide → 2-[4-(1,3-Dithiolan-2-ylideneamino)phenyl]butanol

HRID 1074447Notes

Reaction equation

HRID 1074447 reaction equation
CN(C)C=O.C(N(CC)CC)C.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH2:23][CH3:24])[CH2:21][OH:22])=[CH:16][CH:15]=1.[I-].C[S+]=[C:28]1[S:32][CH2:31][CH2:30][S:29]1>C(OCC)C>[S:29]1[CH2:30][CH2:31][S:32][C:28]1=[N:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH2:23][CH3:24])[CH2:21][OH:22])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 131457182-(4-Aminophenyl)butanolHCID 71374398(1,3-Dithiolan-2-ylidene)(methyl)sulfanium iodide

Product 1

HCID 131457192-[4-(1,3-Dithiolan-2-ylideneamino)phenyl]butanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 450 ml of dimethylformamide containing 23.8 ml of triethylamine was added 11.4 g of 2-(4-aminophenyl)-butanol and to the resulting solution was added, in portions over 45 minutes, 21 g of methyl(1,3-dithiolan-2-ylidene)sulfonium iodide. The resulting hazy-yellow solution was stirred for 2 hours and then poured into ice water. The aqueous mixture was extracted 5 times with diethyl ether and the combined organic extracts were washed 7 times with 0.2 N hydrochloric acid, twice with water and once with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was evaporated and the resulting crude residue was purified by chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane. The purified light-yellow oil obtained was immediately dissolved in warm diethyl ether and allowed to crystallize. The solid which formed was separated by filtration and dried to give 2-[4-(1,3-dithiolan-2-ylideneamino)phenyl]butanol as white spars melting at about 98.5°-100.5° C. This compound has the following structural formula ##STR3##

Workup

  1. additionto the resulting solution was added, in portions over 45 minutes
  2. extractionThe aqueous mixture was extracted 5 times with diethyl ether
  3. washthe combined organic extracts were washed 7 times with 0.2 N hydrochloric acid
  4. dry with materialtwice with water and once with saturated aqueous sodium chloride solution and dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting crude residue was purified by chromatography on silica gel
  7. washeluting with 1:1 ethyl acetate/hexane
  8. customThe purified light-yellow oil obtained
  9. customto crystallize
  10. customThe solid which formed
  11. customwas separated by filtration
  12. customdried

Sources & evidence

ORD record
ord-6dd39eacc36144babc54687108e4218a
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Reaction notes

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