Hydrochloric Acid → HCID 131712110, compound

HRID 127099Notes

Reaction equation

HRID 127099 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7]SC(=N)N)[N:6]=1.[OH-].[Na+].Cl.NC1[S:17]C=C(CS)N=1.[CH3:23][N:24]1[C:28]([S:29][CH2:30][C:31]2[CH2:32][S:33][C@@H:34]3[CH:41]([NH:42][C:43](=O)[CH2:44]Br)[C:40](=[O:47])[N:35]3[C:36]=2[C:37]([OH:39])=[O:38])=[N:27][N:26]=[N:25]1.C(=O)(O)[O-].[Na+]>C(O)C.O>[CH3:23][N:24]1[C:28]([S:29][CH2:30][C:31]2[CH2:32][S:33][C@@H:34]3[CH:41]([NH:42][C:43](=[S:17])[CH2:44][CH2:7][C:5]4[N:6]=[C:2]([NH2:1])[S:3][CH:4]=4)[C:40](=[O:47])[N:35]3[C:36]=2[C:37]([OH:39])=[O:38])=[N:27][N:26]=[N:25]1

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 73233(2-Imino-2,3-dihydro-1,3-thiazol-4-yl)methyl carbamimidothioateHCID 516892Sodium BicarbonateHCID 20130112HCID 20130112, compoundHCID 70572016HCID 70572016, compound

Product 1

HCID 131712110HCID 131712110, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(2-aminothiazol-4-ylmethyl)isothiourea (1.57 g.) and 1 N sodium hydroxide (24 ml.) was stirred for 15 minutes at room temperature, and then the mixture was adjusted to pH 9 with 1 N hydrochloric acid (12 ml.). Thus obtained solution containing 2-aminothiazol-4-ylmethanethiol was dropwise added to a mixture of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-bromoacetamido-3-cephem-4-carboxylic acid (2.16 g.), sodium bicarbonate (0.67 g.), water (33 ml.) and ethanol (33 ml.) over 15 minutes at room temperature with stirring. The mixture was stirred for 1 hour at room temperature, and it was adjusted to pH 4 with 1 N hydrochloric acid. The mixture was allowed to stand for overnight in a refrigerator, and the precipitates were collected by filtration, washed with a small amount of water and then dried to give powder of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-(2-aminothiazol-4-yl)methylthioacetamido-3-cephem-4-carboxylic acid (0.7 g.), mp 180° to 250° C. (dec.)

Workup

  1. stirringwith stirring
  2. stirringThe mixture was stirred for 1 hour at room temperature
  3. waitto stand for overnight in a refrigerator
  4. filtrationthe precipitates were collected by filtration
  5. washwashed with a small amount of water
  6. customdried

Sources & evidence

ORD record
ord-74f9edd6201f4b688b517b008f72ced3
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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