Hydrochloric Acid → HCID 178477391, compound

HRID 461230Notes

Reaction equation

HRID 461230 reaction equation
[NH2:1][CH:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:3]([NH:5][CH:6]1[C:24](=[O:25])[N:8]2[C:9]([C:21]([OH:23])=[O:22])=[C:10]([CH:13]([S:15][C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH3:14])[CH2:11][S:12][C@H:7]12)=[O:4].[O:32]=[C:33]1[N:37]([C:38](Cl)=[O:39])[C:36]2[CH:41]=[CH:42][CH:43]=[CH:44][C:35]=2[NH:34]1.Cl>C(#N)C>[O:32]=[C:33]1[N:37]([C:38]([NH:1][CH:2]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:3]([NH:5][CH:6]2[C:24](=[O:25])[N:8]3[C:9]([C:21]([OH:23])=[O:22])=[C:10]([CH:13]([S:15][C:16]4[NH:20][N:19]=[N:18][N:17]=4)[CH3:14])[CH2:11][S:12][C@H:7]23)=[O:4])=[O:39])[C:36]2[CH:41]=[CH:42][CH:43]=[CH:44][C:35]=2[NH:34]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 105840642,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chlorideHCID 178477389HCID 178477389, compound

Product 1

HCID 178477391HCID 178477391, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 15 ml. of dry acetonitrile were added 923 mg. (2 mmoles of 7-(α-aminophenylacetamido)-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 1.62 grams (8 mmoles) of N,O-bis-trimethylsilylacetamide. Solution was complete within 5 minutes. To the mixture then were added 452 mg. (2.3 mmoles) of 2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride. The temperature of the mixture rose about 4°and solution was complete within 5 minutes. After 20 minutes, a sample of the reaction mixture, analyzed by TLC, indicated that the reaction was complete. After two hours, the mixture (containing some solid) was slowly dropped into rapidly stirred ice water. A gummy solid deposited and was changed to particulate solid upon further stirring of the mixture. The suspension (pH 1.9) was adjusted to pH 1.7 by addition of concentrated hydrochloric acid. The mixture was filtered, and the solid was washed with dilute hydrochloric acid and air-dried to give 1.16 grams of the title compound as a buff-colored powder.

Workup

  1. additionTo the mixture then were added 452 mg
  2. waitwas complete within 5 minutes
  3. waitAfter 20 minutes
  4. waitAfter two hours
  5. additionthe mixture (containing some solid)
  6. filtrationThe mixture was filtered
  7. washthe solid was washed with dilute hydrochloric acid
  8. customair-dried

Sources & evidence

ORD record
ord-88363e17250441c28cac049162809f15
Source dataset
uspto-grants-1977_12
Patent number
US04061861

Reaction notes

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