Tris(hydroxymethyl)aminomethane → HCID 131716326, compound

HRID 1164777Notes

Reaction equation

HRID 1164777 reaction equation
[NH2:1][C:2]([CH2:7][OH:8])([CH2:5][OH:6])[CH2:3][OH:4].[CH2:9]1[CH2:16][CH2:15][O:14][C:12](=[O:13])[CH2:11][CH2:10]1.OC1OCCN=1>>[CH2:9]1[CH2:16][CH2:15][O:14][C:12](=[O:13])[CH2:11][CH2:10]1.[CH2:3]([OH:4])[C:2]([NH2:1])([CH2:7][OH:8])[CH2:5][OH:6]

Participants

4

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 10401epsilon-CAPROLACTONE2×HCID 739492-Oxazolidinone

Product 1

HCID 131716326HCID 131716326, compound

Conditions

Temperature
150 °C

Procedure

About 121.0 g (1.0 mole) of 2-amino-2-(hydroxymethyl)-1,3-propanediol (THAM) was combined with 114.0 g (1.0 mole) of E-Caprolactone and 0.1 g stannous octanoate Sn(OCT)2. As the reaction mixture was slowly heated to 150° C., a clear solution was obtained. Infrared analysis of the reaction product showed no unreacted caprolactone. Upon heating the product cyclized to a hydroxy-oxazoline, and a strong absorption band at 6.0 microns in the infrared spectrum was observed. The product analyzed for 50.94% C, 9.29% H and 5.79% N.

Workup

  1. customa clear solution was obtained
  2. temperatureUpon heating the product

Sources & evidence

ORD record
ord-ecaff8498afe40aeae5790b8a89fb720
Source dataset
uspto-grants-1990_03
Patent number
US04906394

Reaction notes

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