Water → HCID 12926157, compound

HRID 615159Notes

Reaction equation

HRID 615159 reaction equation
Br.[NH:2]=[C:3]1[N:7]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[S:4]1.[BH4-].[Na+].O.[ClH:24].C(O)C>C(O)C>[ClH:24].[NH:2]=[C:3]1[N:7]([CH2:8][CH:9]([OH:10])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[S:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11624441HCID 11624441, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 12926157HCID 12926157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 100 ml of ethanol was suspended 7.5 g of 2-imino-3-phenacyl-2,3-dihydrobenzothiazole hydrobromide and after cooling the suspension to 0° C. to 5° C., 1.2 g of sodium borohydride was gradually added to the suspension, and the mixture was stirred for one hour. The reaction mixture was mixed with 5 ml of water and concentrated under reduced pressure. The residue was extracted with toluene and the extract was washed with water, dried with anhydrous magnesium sulfate, and then the solvent was distilled off to provide a tacky residue. The tacky product was dissolved in ethanol and hydrochloric acid-ethanol was added to the solution to provide 6 g of 2-imino-3-(β-hydroxyphenethyl)-2,3-dihydrobenzothiazole hydrochloride. Melting point: 253°-255° C.

Workup

  1. temperatureafter cooling the suspension to 0° C. to 5° C.
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue was extracted with toluene
  4. washthe extract was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto provide a tacky residue

Sources & evidence

ORD record
ord-28883423b30a476494247be76ca9c648
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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