Hydrochloric Acid → Cephradine Dimethylformamide

HRID 1197758

Reaction equation

HRID 1197758 reaction equation
[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:19])[C:13]3[CH2:18][CH:17]=[CH:16][CH2:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23].Cl>>[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:19])[C:13]3[CH2:18][CH:17]=[CH:16][CH2:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23].[CH3:3][N:4]([CH3:5])[CH:7]=[O:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 38103Cephradine

Product 1

HCID 86747480Cephradine Dimethylformamide

Procedure

To an aqueous solution of about 270 ml, containing approximately 49 g of cephradine in the form of its hydrochloride, (and obtained, after extraction from any suitable reaction mixture of cephradine) 340 ml of dimethylformamide were added, the temperature being maintained at below 35°. The pH was adjusted to 4.3 by addition of ammonia at 30°-35° C. and the mixture was stirred for several minutes as precipitation commenced. The pH was further adjusted to 6.6 with ammonia at 30° to 35° and the slurry was then cooled to 20° to 25° and filtered. The cake was washed with 160 ml of DMF and 130 ml of acetone to obtain the heading compound.

Workup

  1. custom(and obtained
  2. extractionafter extraction
  3. additionfrom any suitable reaction mixture of cephradine) 340 ml of dimethylformamide
  4. additionwere added
  5. temperaturethe temperature being maintained at below 35°
  6. additionThe pH was adjusted to 4.3 by addition of ammonia at 30°-35° C.
  7. customwas further adjusted to 6.6 with ammonia at 30° to 35°
  8. temperaturethe slurry was then cooled to 20° to 25°
  9. filtrationfiltered
  10. washThe cake was washed with 160 ml of DMF and 130 ml of acetone
  11. customto obtain the heading compound

Sources & evidence

ORD record
ord-a088a6328e35403e89a43b8f09949c8c
Source dataset
uspto-grants-1994_01
Patent number
US05278157

Linked notes

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