Bismuth trichloride → HCID 68992465, compound

HRID 2109358Notes

Reaction equation

HRID 2109358 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10]([CH:12]2[N:16]3[C:17](=[O:21])[C:18](Br)([Br:19])[C@H:15]3[S:14](=[O:22])[C:13]2([CH3:24])[CH3:23])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C(OC(C2N3C(=O)C(Br)(Br)[C@H]3S(=O)C2(C)C)=O)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+].[Bi](Cl)(Cl)Cl.[Al]>ClCCl.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([CH:12]2[N:16]3[C:17](=[O:21])[CH:18]([Br:19])[C@H:15]3[S:14](=[O:22])[C:13]2([CH3:23])[CH3:24])=[O:11])=[CH:25][CH:26]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 24591Bismuth trichlorideHCID 25517Ammonium ChlorideHCID 5359268AluminumHCID 14096412HCID 14096412, compoundHCID 68994234HCID 68994234, compound2×

Product 1

HCID 68992465HCID 68992465, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A 82.6 g quantity of 6,6-dibromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide p-nitrobenzyl ester (Compound 4) [compound of the formula (1) wherein X═Y═Br, R=p-nitrobenzyl, n=1] was dissolved in 300 mL of dichloromethane. To the solution was added 115 mL of 20% aqueous solution of ammonium chloride and 36 mL of methanol with stirring. After adding 1.6 g of bismuth chloride and 10 g of aluminum powder at one time, the mixture was reacted at 40° C. for 8 hours. An organic layer was separated and concentrated by an evaporator to give 6-bromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide p-nitrobenzyl ester (Compound 5) [compound of the formula (1b) wherein X═Br, Y═H, R=p-nitrobenzyl, n=1] in a yield of 65%.

Workup

  1. customthe mixture was reacted at 40° C. for 8 hours
  2. customAn organic layer was separated
  3. concentrationconcentrated by an evaporator

Sources & evidence

ORD record
ord-e74d3d2db1b343989c3bbbd1f5346907
Source dataset
uspto-grants-2009_04
Patent number
US07514553B2

Reaction notes

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