Sodium Hydroxide → 3-Methylbenzene-1,2,4,5-tetramine

2,3,5,6-Tetraaminotoluene tetrahydrochloride (TAT.4HCl) aqueous solution (100 g) obtained from Example 1 (equivalent to 29.8 g of 1,6-diamino-3,5-dinitrotoluene) was added to a 500 mL vessel along with tin powder (0.401 g, 3.375 mmol). This mixture was stirred for 10 minutes. NaOH (27 g, 675 mmol) was added to 45 mL of deaerated water, allowed to cool to room temperature and then added to the stirring TAT.4HCl solution to form a reaction mixture. The reaction mixture was stirred for 30 minutes and free base TAT precipitated out of solution as the reaction mixture was cooled down to 15° C. The precipitate was recovered by filtration, and washed with deaerated water (20 mL) and deaerated methanol (20 mL). This wet cake was used for Examples 6 and 7. A dried sample of the precipitate revealed the overall yield of the crystalline white solid to be 64% yield (10.92 g). 1H-NMR analysis indicated product purity was >99%.

1. additionadded to the stirring TAT.4HCl solution
2. customto form a reaction mixture
3. stirringThe reaction mixture was stirred for 30 minutes
4. customfree base TAT precipitated out of solution as the reaction mixture
5. temperaturewas cooled down to 15° C
6. filtrationThe precipitate was recovered by filtration
7. washwashed with deaerated water (20 mL) and deaerated methanol (20 mL)

ORD record

ord-c38308d71b3745c9b167c1f4778feb3c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188316B2