3-Bromo-5,6-dimethoxy-phthalide → 5,6-Dimethoxyphthalide benzylpenicillin

HRID 1578767Notes

Reaction equation

HRID 1578767 reaction equation
[K].[CH3:2][C:3]1([CH3:24])[S:7][C@@H:6]2[C@H:8]([NH:11][C:12]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:13])[C:9](=[O:10])[N:5]2[C@H:4]1[C:21]([OH:23])=[O:22].Br[CH:26]1[C:35]2[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=2)[C:28](=[O:29])[O:27]1>O>[CH3:37][O:36][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][C:32]=1[O:38][CH3:39])[C:28](=[O:29])[O:27][CH2:26]2.[CH3:2][C:3]1([CH3:24])[S:7][C@@H:6]2[C@H:8]([NH:11][C:12]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:13])[C:9](=[O:10])[N:5]2[C@H:4]1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 111965723-Bromo-5,6-dimethoxy-phthalideHCID 66586213CID 66586213

Product 1

HCID 1317100375,6-Dimethoxyphthalide benzylpenicillin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium-benzylpenicillin (2.73 g., 0.00734 mole) was stirred in dry D.M.F. (100 ml.) with 3-bromo-5,6-dimethoxyphthalide (2.0 g., 0.00734 mole) for 12 hours. The mixture was poured into iced water (2 lits) with vigorous stirring and the solid filtered, dried and crystallised from isopropanol.

Workup

  1. filtrationthe solid filtered
  2. customdried
  3. customcrystallised from isopropanol

Sources & evidence

ORD record
ord-de869175b02d4de1abc455cca8aa37f9
Source dataset
uspto-grants-1976_02
Patent number
US03939180

Reaction notes

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