Hydrochloric Acid → HCID 54556098, compound

HRID 2296033Notes

Reaction equation

HRID 2296033 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](Cl)=[O:7])[N:3]=[N:2]1.[CH3:9][O:10][C:11](=[O:26])[C@H:12]([CH3:25])[NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH3:24].Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:9][O:10][C:11](=[O:26])[C@H:12]([CH3:25])[N:13]([C:6]([C:4]1[N:3]=[N:2][S:1][CH:5]=1)=[O:7])[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 64854301,2,3-thiadiazole-4-carbonyl chlorideHCID 53685327HCID 53685327, compound

Product 1

HCID 54556098HCID 54556098, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

14 g (0.095 mole) of 1,2,3-thiadiazole-4-carbonyl chloride in 30 ml of toluene were added dropwise to a solution of 22.9 g (0.0945 mole) of N-(2-methyl-1-naphthyl)-alanine methyl ester in 100 ml of dry toluene at from +15° C. to +30° C. The mixture was stirred at 80° C. for 8 hours, during which the hydrogen chloride formed was continuously expelled in a weak stream of nitrogen. The mixture was cooled and stirred with a solution of 5 g of sodium bicarbonate in 100 ml of water. The organic phase was separated off, dried over sodium sulfate, decolorized with charcoal and evaporated under reduced pressure. The oily residue which remained was dried at 50° C. and under 0.1 mbar for 3 hours to give 32 g (95.2% of theory) of N-(1,2,3-thiadiazol-4-yl-carbonyl)-N-(2-methyl-1-naphthyl)-alanine methyl ester as a light-brown resin.

Workup

  1. customformed
  2. temperatureThe mixture was cooled
  3. customThe organic phase was separated off
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe oily residue which remained was dried at 50° C. and under 0.1 mbar for 3 hours

Sources & evidence

ORD record
ord-7303a20803374d219a7fc96e15372a63
Source dataset
uspto-grants-1984_01
Patent number
US04427688

Reaction notes

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