Dimethyl Sulfoxide → Amoxicillin Dimethyl Sulfoxide

HRID 866968

Reaction equation

HRID 866968 reaction equation
[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:21])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23].O.O.O.[CH3:29][S:30]([CH3:32])=[O:31].O.CC1(C)S[C@@H]2[C@H](NC([C@H](N)C3C=CC(O)=CC=3)=O)C(=O)N2[C@H]1C(O)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:21])[C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23].[CH3:29][S:30]([CH3:32])=[O:31]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 33613AmoxicillinHCID 62883Amoxicillin Trihydrate

Product 1

HCID 70528119Amoxicillin Dimethyl Sulfoxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fifty grams of amoxicillin trihydrate is added in portions, with stirring, to 375 ml. of dimethyl sulfoxide. The mixture is stirred at room temperature for 2 hours, then diluted with 75 ml. of methylene chloride and cooled to 0°-5°. The solid product is collected by filtration, washed with methylene chloride and dried. Analysis shows 3 moles of dimethyl sulfoxide and 0.5 mole of water for each mole of amoxicillin; formula weight = 609.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. additiondiluted with 75 ml
  3. filtrationThe solid product is collected by filtration
  4. washwashed with methylene chloride
  5. customdried

Sources & evidence

ORD record
ord-6a641e2172144ef89d40daebb7862663
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Linked notes

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