Acetic Acid → HCID 15017643, compound

HRID 2247935Notes

Reaction equation

HRID 2247935 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-db1f391f97f349279173f01d8361f2c0
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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