Hydrochloric Acid → HCID 178427282, compound

HRID 370823Notes

Reaction equation

HRID 370823 reaction equation
[NH2:1][C:2]1[C:6]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]2[S:13][C:14]([CH2:18][N:19]([CH3:21])[CH3:20])=[C:15]([CH3:17])[CH:16]=2)=[N:5]S(=O)[N:3]=1.[ClH:23]>CO>[ClH:23].[ClH:23].[ClH:23].[CH3:21][N:19]([CH2:18][C:14]1[S:13][C:12]([CH2:11][S:10][CH2:9][CH2:8][NH:7][C:6](=[NH:5])[C:2](=[NH:1])[NH2:3])=[CH:16][C:15]=1[CH3:17])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23312524HCID 23312524, compound

Product 1

HCID 178427282HCID 178427282, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 3-amino-4-{2-[(5-dimethylaminomethyl-4-methyl-2-thienyl)methylthio]ethylamino}-1,2,5-thiadiazole 1-oxide (17.9 g, 50.0 mmoles) [prepared according to the general procedure described in published U.K. patent application No. 2,067,987] in 500 mL of methanol was treated with 33.3 mL of concentrated HCl. After stirring for 3 hours, the reaction mixture was concentrated and excess water was removed by azeotropic concentration with absolute ethanol to give an almost colorless crystalline residue. The residue was triturated with 200 mL of absolute ethanol at 0° C., filtered and dried to give 16.9 g (80%) of the title compound, m.p. 206°-220° C. (dec.). Recrystallization from 50% methanol-ethyl acetate gave a product having m.p. 210°-221° C. (dec.).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customexcess water was removed by azeotropic concentration with absolute ethanol
  3. customto give an almost colorless crystalline residue
  4. customThe residue was triturated with 200 mL of absolute ethanol at 0° C.
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-485f8264314a48b8bc6ea625b5fc1a67
Source dataset
uspto-grants-1985_07
Patent number
US04528378

Reaction notes

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