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Sodium nitrite hydrate → HCID 178427241, compound

HRID 261843
Notes
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Reaction equation

HRID 261843 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:5]2[C:16](=[O:26])[CH:17]([NH:18][C:19](=[O:25])[CH2:20][C:21](=[O:24])[CH2:22][Br:23])[C@H:4]2[S:3]1.O.[N:28]([O-])=[O:29].[Na+]>C(O)(=O)C.O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][C:12]([Cl:13])([Cl:15])[Cl:14])=[O:9])[N:5]2[C:16](=[O:26])[CH:17]([NH:18][C:19](=[O:25])[C:20](=[N:28][OH:29])[C:21](=[O:24])[CH2:22][Br:23])[C@H:4]2[S:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23686037Sodium nitrite hydrateHCID 1317114902,2,2-Trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

Product 1

HCID 178427241HCID 178427241, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (2.54 g.) in glacial acetic acid (25 ml.) was added dropwise a solution of sodium nitrite hydrate (0.33 g.) in water (1 ml.) over 3 minutes with stirring at 10° to 15° C., and then the mixture was stirred for 1 hour at the same temperature. After the reaction mixture was poured into cold water (70 ml.), the precipitates were collected by filtration and then dried to give brown powder of 2,2,2-trichloroethyl 2-methyl-7-(2-hydroxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (a mixture of syn and anti isomers) (2.0 g.), mp 76° to 80° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. filtrationthe precipitates were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-ac05ae580eba4dbab9fd6836fb723769
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04152433

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes