Hydrochloric Acid → 2-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethylamine

HRID 49383

Reaction equation

HRID 49383 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20]C(=O)C)=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH2:20])=[CH:16][CH:17]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9343045N-[2-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethyl}-acetamide

Product 1

HCID 185236422-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethylamineYield 85%

Conditions

Temperature
120 °C

Procedure

In a round-bottomed flask, N-{2-[4-(2-phenyl-thiazol-4-yl)-phenyl]-ethyl}-acetamide (838 mg, 2.60 mmol) was added to 5.0 ml of concentrated HCl and the resulting solution was heated to about 120° C. for about sixteen hours. The solution was then cooled to about 0° C., brought to pH 12 with 5M sodium hydroxide, and extracted with four portions of methylene chloride. The combined organic extracts were then washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The crude material was purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride) to afford the product (617 mg, 85% yield). LRMS ([M+H]+)=281.2.

Workup

  1. temperatureThe solution was then cooled to about 0° C.
  2. extractionextracted with four portions of methylene chloride
  3. washThe combined organic extracts were then washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (silica gel; methylene chloride to 20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-f6dc22ce7e034bc1be1448ef773ce304
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Linked notes

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