Hydrochloric Acid → HCID 19069533, compound

HRID 1379759Notes

Reaction equation

HRID 1379759 reaction equation
O.Cl.C[O:4][CH:5](OC)[CH2:6][CH2:7][CH2:8][NH:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH:20](OC)[O:21]C)[N:13]=[C:12]([NH:25][CH2:26][CH2:27][CH2:28][CH:29]([O:32]C)OC)[N:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:32][CH:29]1[CH2:28][CH2:27][CH2:26][N:25]1[C:12]1[N:13]=[C:14]([N:16]2[CH2:17][CH2:18][CH2:19][CH:20]2[OH:21])[N:15]=[C:10]([N:9]2[CH2:8][CH2:7][CH2:6][CH:5]2[OH:4])[N:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 19069522HCID 19069522, compound

Product 1

HCID 19069533HCID 19069533, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Water (50 ml) containing 37 weight % hydrochloric acid (6 ml) was added in one portion to a stirred solution of the tris-(4,4-dimethoxybutylamino)-1,3,5-triazine of Example 1 (6.0 g; 0.0127 mole) in acetone (50 ml) under nitrogen. The reaction mixture was stirred at room temperature for four days and thereafter neutralized with solid potassium carbonate. The solution was then transferred to a separatory funnel and extracted with ethyl acetate (2×150 ml). The organic layer was separated, dried over anhydrous sodium sulfate and the volatiles were removed under reduced pressure to give 2,4,6-tris-(2-hydroxypyrrolidin-1-yl)-1,3,5-triazine as a solid (2.7 g; 64% isolated yield). The structure of the product was confirmed from the 1H NMR spectrum which exhibited the characteristic absorption for the --NCHO-- group at (δ) 5.6 (m, 1H).

Workup

  1. customThe solution was then transferred to a separatory funnel
  2. extractionextracted with ethyl acetate (2×150 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe volatiles were removed under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-a65a601d680443c8bcfffbf15ee21b65
Source dataset
uspto-grants-1997_09
Patent number
US05672703

Reaction notes

Loading…