Methylhydrazine → HCID 12796638, compound

HRID 1414342Notes

Reaction equation

HRID 1414342 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.C(N(CC)CC)C.ClC(OCC)=O.CNN>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 4

HCID 6061MethylhydrazineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 70633162HCID 70633162, compound

Product 1

HCID 12796638HCID 12796638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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. filtrationThe Et3N.HCl 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-2019f723b9444485a83032c18e70b678
Source dataset
uspto-grants-1977_01
Patent number
US04001239

Reaction notes

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