Methylhydrazine → HCID 12796638, compound

HRID 1730906Notes

Reaction equation

HRID 1730906 reaction equation
C(C1C=CC=CC=1C([NH:8][CH:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:13]([CH2:16][S:17][C:18]3[S:19][C:20]([CH3:23])=[N:21][N:22]=3)[CH2:14][S:15][C@H:10]12)=O)(O)=O.ClC(OCC)=O.CNN>CCN(CC)CC.O1CCCC1>[NH2:8][CH:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:13]([CH2:16][S:17][C:18]3[S:19][C:20]([CH3:23])=[N:21][N:22]=3)[CH2:14][S:15][C@H:10]12

Participants

6

Reactant 3

HCID 6061MethylhydrazineHCID 10928Ethyl chloroformateHCID 70633162HCID 70633162, compound

Product 1

HCID 12796638HCID 12796638, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

A solution of benzhydryl 7-(2-carboxybenzamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate (2 mmol.) in 30 ml. of dry tetrahydrofuran is cooled in an ice-salt bath, and 0.28 ml. (2 mmol.) of triethylamine and 0.20 ml. (2. mmol.) of ethyl chloroformate are added. After cooling and stirring for 20 minutes, 0.106 ml. (2 mmol.) of N-methylhydrazine in 5 ml. of tetrahydrofuran is added. Stirring is continued for about 10 minutes. The Et3N. HCl salt is filtered, and the filtrate is evaporated to dryness. The residue is taken up in about 15 ml. of chloroform, and the mixture is allowed to stand at room temperature for about one hour during which time methylphthalhydrazide (m,p, 243°-245° C.) precipitates. Filtration and evaporation in vacuo of the filtrate gives crude benzhydryl 7-amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate.

Workup

  1. temperatureAfter cooling
  2. stirringStirring
  3. waitis continued for about 10 minutes
  4. filtrationHCl salt is filtered
  5. customthe filtrate is evaporated to dryness
  6. waitto stand at room temperature for about one hour during which time methylphthalhydrazide (m,p, 243°-245° C.)
  7. customprecipitates
  8. filtrationFiltration and evaporation in vacuo of the filtrate

Sources & evidence

ORD record
ord-2b8440cca3d640a59af5de647a98bc1c
Source dataset
uspto-grants-1976_11
Patent number
US03994888

Reaction notes

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