Cysteamine Hydrochloride → HCID 15592298, compound

HRID 1758668Notes

Reaction equation

HRID 1758668 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].Cl.[CH3:7][N:8]=[C:9]([NH2:18])[NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16]Cl)[N:15]=1>Cl>[CH3:7][N:8]=[C:9]([NH2:18])[NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][S:5][CH2:4][CH2:3][NH2:2])[N:15]=1

Participants

4

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 20402114HCID 20402114, compound

Product 1

HCID 15592298HCID 15592298, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Cysteamine hydrochloride (1.89 g; 16.6 mmoles) and 2-(2-methylguanidino)-4-chloromethylthiazole hydrochloride (4.0 g; 16.6 mmoles) [prepared from (N-methylamidino)thiourea and 1,3-dichloro-2-propanone] were combined in 20 ml of concentrated hydrochloric acid and the solution was heated at an oil bath temperature of 100°. After 2 hours the mixture was evaporated under reduced pressure and the residue made basic with 40% aqueous NaOH solution. The aqueous phase was extracted several times with methyl acetate and the organic phase was dried, filtered and evaporated to give 3.35 g of the title compound. The NMR spectrum (60 MHz) in D2O gave the following characteristic resonances δ: 6.52 (s, 1H), 3.60 (s, 2H), 2.70 (m, 7H).

Workup

  1. temperaturethe solution was heated at an oil bath temperature of 100°
  2. customAfter 2 hours the mixture was evaporated under reduced pressure
  3. extractionThe aqueous phase was extracted several times with methyl acetate
  4. customthe organic phase was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f08d22564df04006a57d0f54691317e5
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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