Water → HCID 12773912, compound

HRID 1164538Notes

Reaction equation

HRID 1164538 reaction equation
[ClH:1].[OH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[CH2:6][CH2:7][NH2:8].C(O[CH:16](OCC)[CH2:17][O:18][C:19]1[CH:23]=[N:22][S:21][N:20]=1)C.O>Cl.C(O)CCC>[ClH:1].[S:21]1[N:22]=[CH:23][C:19]([O:18][CH2:17][CH:16]2[C:9]3[C:5](=[CH:4][C:3]([OH:2])=[C:11]([OH:12])[CH:10]=3)[CH2:6][CH2:7][NH:8]2)=[N:20]1

Participants

6

Reactant 3

HCID 962WaterHCID 65340Dopamine HydrochlorideHCID 20511267HCID 20511267, compound

Product 1

HCID 12773912HCID 12773912, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 2631-ButanolSolvent2×

Procedure

A mixture of 3,4-dihydroxyphenethylamine hydrochloride (1.62 g), (1,2,5-thiadiazol-3-yl)oxyacetaldehyde diethyl acetal (2.6 g), n-butanol (50 ml), water (25 ml) and 10% hydrochloric acid (3 drops) was refluxed for 15 hours. After the reaction, n-butanol was distilled off from the reaction mixture under reduced pressure. The residue was dissolved in water, and the solution was washed twice with chloroform and once with ether and then the aqueous layer was concentrated to give colourless crystals of 1-(1,2,5-thiadiazol-3-yl)oxymethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2 g). The product was recrystallized from aqueous methanol to give colourless crystals like cotton, mp 252° C. (dec.).

Workup

  1. temperaturewas refluxed for 15 hours
  2. distillationwas distilled off from the reaction mixture under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washthe solution was washed twice with chloroform and once with ether
  5. concentrationthe aqueous layer was concentrated

Sources & evidence

ORD record
ord-2178a5558e68452aa126ed19a1de6973
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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