Cefonicid → Benzathine

HRID 724796Notes

Reaction equation

HRID 724796 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@@H:7](O)C(N[C@@H]2C(=O)N3C(C(O)=O)=C(CSC4N(CS(O)(=O)=O)N=NN=4)CS[C@H]23)=O)=[CH:5][CH:6]=1.C(O)(=O)C.C(O)(=O)C.[CH2:44]([N:51](CC1C=CC=CC=1)[CH2:52][CH2:53][NH2:54])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O.CO>[CH2:44]([NH:51][CH2:52][CH2:53][NH:54][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 2

HCID 43594CefonicidHCID 22215064HCID 22215064, compound

Product 1

HCID 8793BenzathineYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of cefonicid (5.76 g, 9.8 mmol) in water (6.3% w/w), at pH 5-6 and ambient temperature, methanol (50 ml) was added, followed by a suspension of N,N-dibenzylethylene diamine diacetate (8.6 g, 24 mmol) in methanol (50 ml). The reaction mixture was stirred for 3 h at 20°-25° C., resulting in formation of a white solid. The reaction mixture was cooled to 10°-15° C. and filtered. The white solid was washed with water (3×15 ml) and methanol (3×10 ml). The solid was dried at 30°-35° C. under vacuum. (7.63 g, 99.4% yield). The melting range of the crystals was 191°-193° C. Washed salt with water (50 ml×2) followed by methanol (120 ml) to yield a product with a melting range of 195°-198° C. Elemental Analysis (C34H38N8 O8S3) calcd: C, 52.16; H, 4.89; N, 14.31; S, 12.26. found: C, 52.06; H, 4.89; N, 14.01; S, 12.27.

Workup

  1. customresulting in formation of a white solid
  2. temperatureThe reaction mixture was cooled to 10°-15° C.
  3. filtrationfiltered
  4. washThe white solid was washed with water (3×15 ml) and methanol (3×10 ml)
  5. customThe solid was dried at 30°-35° C. under vacuum
  6. customwas 191°-193° C
  7. customto yield a product with a melting range of 195°-198° C

Sources & evidence

ORD record
ord-92cdcda0066b478dac7df98e4a4cead8
Source dataset
uspto-grants-1998_01
Patent number
US05705496

Reaction notes

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