Water → HCID 19750885, compound

HRID 485391Notes

Reaction equation

HRID 485391 reaction equation
C([O:4][CH2:5][C:6]([N:8]=[C:9]([NH:20][CH2:21][CH2:22][S:23][CH2:24][C:25]1[O:26][C:27]([CH2:30][N:31]([CH3:33])[CH3:32])=[CH:28][CH:29]=1)[N:10]([CH3:19])[N:11]=CC1C=CC=CC=1)=O)(=O)C.O>Cl>[NH3:8].[CH3:32][N:31]([CH2:30][C:27]1[O:26][C:25]([CH2:24][S:23][CH2:22][CH2:21][NH:20][C:9]2[N:10]([CH3:19])[N:11]=[C:6]([CH2:5][OH:4])[N:8]=2)=[CH:29][CH:28]=1)[CH3:33]

Participants

5

Reactant 2

HCID 962WaterHCID 178476502HCID 178476502, compound

Product 2

HCID 222AmmoniaHCID 19750885HCID 19750885, compoundYield 137.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(acetyloxy)-N-[[[2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]amino][1-methyl-2-(phenylmethylene)hydrazino]methylene]acetamide (0.74 g) in 2N hydrochloric acid was heated at 98°-100° for 1 h. Water (5 ml) was added to the cooled solution which was washed with ethyl acetate. The aqueous fraction was made alkaline with sodium carbonate and the solution was evaporated to dryness in vacuo. The residue was suspended in ethyl acetate (20 ml), excess anhydrous sodium carbonate and decolourising charcoal were added. The suspension was boiled for 10 mins, cooled, filtered and the filtrate was evaporated in vacuo. The residual oil was chromatographed on silica using methanol:0.88 ammonia, (79:1) to give the title compound (0.35 g) as a pale brown oil.

Workup

  1. washwas washed with ethyl acetate
  2. customthe solution was evaporated to dryness in vacuo
  3. additionwere added
  4. temperaturecooled
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residual oil was chromatographed on silica

Sources & evidence

ORD record
ord-92e01fadb9f346a3b1290b486bdcfa1f
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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