Acetic Acid → HCID 15017643, compound

HRID 249303Notes

Reaction equation

HRID 249303 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[S:4][CH:5]=[C:6]([CH2:8][CH2:9][NH2:10])[N:7]=1.C=O.[C:14](O)(=O)C>O.CO>[CH3:11][N:2]([CH3:1])[C:3]1[S:4][C:5]2[CH2:14][NH:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 712Formaldehyde2×HCID 15017654124458-20-4

Product 1

HCID 15017643HCID 15017643, compoundYield 219.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Dimethylamino-4-(2-aminoethyl)thiazole (1.7 g, see preceding preparation), formaldehyde (0.78 ml of a 37% solution in water, 9.6 mmol) and acetic acid (0.15 ml, 2.6 mmol) were combined in methanol (100 ml). After 2.5 hours at room temperature, the reaction mixture was treated with additional formaldehyde (0.15 ml, 1.8 mmol) and allowed to stir for an additional 16 hours. The reaction was then filtered, and the filtrate was concentrated in vacuo and purified by column chromatography (eluant: 89:10:1 of chloroform:methanol:concentrated ammonium hydroxide), providing the title product as a white solid (1.04 g, 5.7 mmol).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by column chromatography (eluant: 89:10:1 of chloroform:methanol:concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-cba5fcd9d46d46cdb9c7eca0684ae0fa
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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