Potassium thiocyanate → HCID 21426468, compound

HRID 258773Notes

Reaction equation

HRID 258773 reaction equation
C(O[CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:24])[CH:10]2[NH:14][C:15](=[O:23])[CH2:16][C:17]2[S:18][C:19](=[O:22])[S:20][CH:21]=2)[C:7]=1[C:25]([OH:27])=[O:26])(=O)C.C(=O)(O)[O-].[Na+].[C:33]([NH:36][CH:37]1[S:41][C:40](=[S:42])[N:39]=[N:38]1)(=[O:35])[CH3:34].[S-]C#N.[K+]>O>[C:33]([NH:36][C:37]1[S:41][C:40]([S:42][CH2:5][C:6]2[CH2:13][S:12][CH:11]3[N:8]([C:9](=[O:24])[CH:10]3[NH:14][C:15](=[O:23])[CH2:16][C:17]3[S:18][C:19](=[O:22])[S:20][CH:21]=3)[C:7]=2[C:25]([OH:27])=[O:26])=[N:39][N:38]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 21426457HCID 21426457, compoundHCID 21932818HCID 21932818, compound

Product 1

HCID 21426468HCID 21426468, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 3-acetoxymethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo-[4.2.0]-oct-2-ene (12.9 g.) in water (50 cc.), sodium bicarbonate (5.52 g.) and 5-acetylamino-2-thioxo-1,3,4-thiadiazoline (6.3 g.) and potassium thiocyanate (58 g.) is heated to 60° C. for 10 hours. The mixture is allowed to cool and diluted with 1 liter of water. A slight amount of insoluble matter is filtered off on "Supercel" and the filtrate is washed with ethyl acetate (250 cc.), which is discarded. It is brought to pH 2 by adding 4 N hydrochloric acid in the presence of ethyl acetate (250 cc.). A solid (6.3 g.) is filtered off and taken up in boiling methanol (200 cc.). An insoluble material is filtered off and the filtrate is concentrated to dryness under reduced pressure (20 mm.Hg). The solid residue obtained is washed with methanol (5 cc.) to give 3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)-thiomethyl]-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (2.9 g.).

Workup

  1. temperatureto cool
  2. filtrationA slight amount of insoluble matter is filtered off on "Supercel"
  3. washthe filtrate is washed with ethyl acetate (250 cc.), which
  4. additionby adding 4 N hydrochloric acid in the presence of ethyl acetate (250 cc.)
  5. filtrationA solid (6.3 g.) is filtered off
  6. filtrationAn insoluble material is filtered off
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mm.Hg)
  8. customThe solid residue obtained
  9. washis washed with methanol (5 cc.)

Sources & evidence

ORD record
ord-d3483ae9fe064e19a124f72a2de8dee5
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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