Bromhydrol → HCID 12834044, compound

HRID 1763997Notes

Reaction equation

HRID 1763997 reaction equation
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[N:5]1[C:16](=[O:27])[CH:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[CH:25]=[N:24][S:23][N:22]=3)[C@H:4]1[S:3]2.[Br-].[Al+3].[Br-].[Br-]>ClCCl>[CH3:1][CH:2]1[CH:15]=[C:6]([C:7]([O:9][CH2:10][C:11]([Cl:13])([Cl:14])[Cl:12])=[O:8])[N:5]2[C:16](=[O:27])[CH:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[CH:25]=[N:24][S:23][N:22]=3)[C@H:4]2[S:3]1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 70528480HCID 70528480, compound

Product 1

HCID 12834044HCID 12834044, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-{2-(1,2,5-thiadiazol-3-yl)acetamido}-penam-3-carboxylate (16.5 g.) in dried dichloromethane (100 ml.) was gradually dropwise added to a solution of aluminum bromide (17.5 g.) in dichloromethane (100 ml.) at below -10° C. Then, the mixture was stirred for 2 hours at below 0° C. and stirred for further 2 hours at room temperature. After the reaction, the reaction mixture was washed in turn with 2% hydrochloric acid (100 ml.) twice, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate. After drying, the solvent was distilled off to give powdery 2,2,2-trichloroethyl 2-methyl-7-{2-(1,2,5-thiadiazol-3-yl)acetamido}-3-cephem-4-carboxylate (13.2 g.), mp 180° to 185° C. (dec.).

Workup

  1. stirringstirred for further 2 hours at room temperature
  2. customAfter the reaction
  3. washthe reaction mixture was washed in turn with 2% hydrochloric acid (100 ml.) twice
  4. dry with materiala saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate
  5. customAfter drying
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-9c9d465243e342a4920bb3a6d4f74dee
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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