1,1'-(Diazomethylene)bis(benzene) → HCID 88777142, compound

HRID 1657422Notes

Reaction equation

HRID 1657422 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]([C:18]1[CH:23]([C:24]([OH:26])=[O:25])[N:22]2[C:27](=[O:38])[CH:28]([NH:29][C:30](=[O:37])[CH2:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C@H:21]2[S:20][CH:19]=1)=[O:17]>O1CCCC1>[CH:16]([C:18]1[CH:23]([C:24]([O:26][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:25])[N:22]2[C:27](=[O:38])[CH:28]([NH:29][C:30](=[O:37])[CH2:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C@H:21]2[S:20][CH:19]=1)=[O:17]

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 88777331HCID 88777331, compound

Product 1

HCID 88777142HCID 88777142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diphenyldiazomethane (0.213 g, 1.1 mmol) in dry tetrahydrofuran (2 ml) was added dropwise with stirring to the 3-formyl-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid (0.352 g., 1 mmol) in dry tetrahydrofuran (10 ml) at 40°. The reagent was allowed to completely react as noted by the color changes between each addition. The reaction was stirred at 40° for 2 hours after the addition was completed and then the solvent was removed in vacuo. The residual oil was dissolved in chloroform, washed with 5% NaHCO3, dried over MgSO4 and concentrated to half volume. The product was precipitated by the addition of hexane.

Workup

  1. customto completely react
  2. additionas noted by the color changes between each addition
  3. additionafter the addition
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residual oil was dissolved in chloroform
  6. washwashed with 5% NaHCO3
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to half volume
  9. customThe product was precipitated by the addition of hexane

Sources & evidence

ORD record
ord-c88c869255de4afb8521078d21ad9050
Source dataset
uspto-grants-1976_06
Patent number
US03960852

Reaction notes

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