OCC[CH:4]([OH:6])[CH3:5].C=O.C(O)[C:10]([NH2:15])(CO)[CH2:11][OH:12].[CH3:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]#[C:27][I:28])=[O:23]>O>[OH:12][CH2:11][CH:10]1[NH:15][CH2:5][CH2:4][O:6]1.[CH2:20]([NH:21][C:22](=[O:23])[O:24][C:25]#[C:26][CH2:27][I:28])[CH2:19][CH2:18][CH3:17]A closed vessel is charged with 102 g of 1,3-dihydroxybutane and 62 g of prilled paraformaldehyde is added and mixed at room temperature until a uniform slurry is formed. The slurry is then heated to 60° C. and a 2% molar (or 1–5%) molar excess of tris(hydroxymethyl)aminomethane (THAM) is introduced. A total of 124 g of 99% pure tris(hydroxymethyl)aminomethane is gradually added in increasing increments until a 2% molar excess is obtained. The ensuing condensation reaction takes place over a period of 3 hours. During the reaction, soluble bicyclic hydroxymethyl oxazolidine is continuously formed. Since paraformaldehyde and tris(hydroxymethyl)-aminomethane are of low solubility in the reaction medium, completion of the reaction is indicated when a clear solution is formed with water by-product. When the mixture becomes clear, insuring that all of the formaldehyde has reacted, the resulting solution is allowed to cool to ambient temperature and 4.42 g of powdered IPBC (weight ratio of bicyclic hydroxymethyl oxazolidine HMBO to IPBC is 33:1) is added and stirred until a clear solution is obtained. No crystallization of IPBC is noted in the substantially colorless product and a pure clear, liquid composition containing less than 1000 ppm of formaldehyde is obtained.
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