2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1) → HCID 59570821, compound

HRID 1685039Notes

Reaction equation

HRID 1685039 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8]Cl)[N:7]=1.Cl.[CH3:11][NH:12][O:13][CH3:14].CCN(C(C)C)C(C)C>C1COCC1>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:12]([O:13][CH3:14])[CH3:11])[N:7]=1

Participants

5

Reactant 3

HCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 59570821HCID 59570821, compoundYield 119.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-4-chloromethyl-thiazole hydrochloride (27.8 g, 0.15 mol), N,O-dimethylhydroxylamine hydrochloride (87.8 g, 0.90 mol), and anhydrous THF (300 mL) was rapidly stirred and DIPEA (157 mL, 0.90 mol) was added. The resulting mixture was heated at 60 C for 10-15 hours. The mixture was cooled in an ice/salt bath and the solid byproduct (DIPEA hydrochloride) was removed by filtration and washed with cold THF (300 mL). The combined filtrate was concentrated to afford the title compound as a dark oil (31 g, >100% theory), which partially crystallized on standing. This product was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was heated at 60 C for 10-15 hours
  2. temperatureThe mixture was cooled in an ice/salt bath
  3. customthe solid byproduct (DIPEA hydrochloride) was removed by filtration
  4. washwashed with cold THF (300 mL)
  5. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-ecdeb2f9ef784275adcf7c26b52be2b8
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

Loading…