Triethylamine → HCID 66859150, compound

HRID 1469978Notes

Reaction equation

HRID 1469978 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:8])[S:5][C:6]=1[CH3:7].Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C>>[CH3:1][C:2]1[N:3]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:4](=[NH:8])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 3

HCID 8471Triethylamine2×HCID 732382-Amino-4,5-dimethyl-1,3-thiazole2×HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 66859150HCID 66859150, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 4,5-dimethyl-thiazol-2-ylamine (1.0 g, 7.8 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (1.6 g, 8.6 mmol) and triethylamine (2.4 mL, 17.2 mmol) were heated at 80° C. After 3 hours, additional triethylamine (1.1 mL, 7.9 mmol) was added and the mixture was stirred at 80° C. for 14 hours, then cooled to ambient temperature and concentrated. The residue was diluted with methylene chloride and washed with saturated aqueous sodium bicarbonate and water. The organic extract was dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide 0.26 g (14%) of a 3:1 mixture of title compound to 4,5-dimethyl-thiazol-2-ylamine. MS (DCI/NH3) m/z 242 (M+H)+.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated
  3. additionThe residue was diluted with methylene chloride
  4. washwashed with saturated aqueous sodium bicarbonate and water
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto provide

Sources & evidence

ORD record
ord-0b0cc87328ec4138b0fd6e269f89f515
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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