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

HRID 2067998Notes

Reaction equation

HRID 2067998 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]([CH3:11])[O:13][CH3:14])[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, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

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 N-(2-amino-thiazol-4-ylmethyl)-O,N-dimethyl-hydroxylamine 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 mixture was cooled in an ice/salt bath
  2. customthe solid byproduct (DIPEA hydrochloride) was removed by filtration
  3. washwashed with cold THF (300 mL)
  4. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-04f232f3292e47009724684518d32c0c
Source dataset
uspto-grants-2012_10
Patent number
US08293919B2

Reaction notes

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