Anisole → HCID 20430437, compound

HRID 2413418Notes

Reaction equation

HRID 2413418 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C([O:18][C:19]([C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[C:29]1[S:33][C:32]([S:34][CH3:35])=[N:31][CH:30]=1)[CH:24]([NH:36][C:37](=[O:44])[CH2:38][C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)[C:23]2=[O:45])=[O:20])(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1>[N+](C)([O-])=O.C(Cl)Cl.C(OCC)(=O)C>[C:19]([C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[C:29]1[S:33][C:32]([S:34][CH3:35])=[N:31][CH:30]=1)[CH:24]([NH:36][C:37](=[O:44])[CH2:38][C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)[C:23]2=[O:45])([OH:20])=[O:18]

Participants

7

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 20430419HCID 20430419, compound

Product 1

HCID 20430437HCID 20430437, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6375NitromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of aluminium chloride (1.04 g) in nitromethane (25 cc) is added in 10 minutes, to a solution, cooled to -8° C., of 2-benzhydryloxycarbonyl-3-(2-methylthiothiazol-5-yl)-8-oxo-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.61 g) in dry methylene chloride (40 cc) containing anisole (4 cc), and the reaction mixture is stirred for 2 hours at a temperature of between -8° C. and 0° C. The reaction mixture is diluted with ethyl acetate (200 cc) and distilled water (200 cc) acidified with 4N hydrochloric acid (3 drops). After filtration to remove insoluble matter, the organic layer is decanted and is washed with distilled water (50 cc) and then extracted with a 5% strength sodium bicarbonate solution (80 cc). The aqueous solution is washed with ethyl acetate (50 cc) and then acidified to pH 3, at 0° C., with 4N hydrochloric acid. The precipitate is filtered off, washed with water (2×20 cc) and dried. 2-Carboxy-3-(2-methylthio-thiazol-5-yl)-8-oxo-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.8 g) is obtained in the form of a white solid.

Workup

  1. distillationdistilled water (200 cc)
  2. filtrationAfter filtration
  3. customto remove insoluble matter
  4. customthe organic layer is decanted
  5. washis washed with distilled water (50 cc)
  6. extractionextracted with a 5% strength sodium bicarbonate solution (80 cc)
  7. washThe aqueous solution is washed with ethyl acetate (50 cc)
  8. customacidified to pH 3, at 0° C., with 4N hydrochloric acid
  9. filtrationThe precipitate is filtered off
  10. washwashed with water (2×20 cc)
  11. customdried

Sources & evidence

ORD record
ord-c8d6e379cb494a4a90ff214995cd22c8
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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