Tris(hydroxymethyl)aminomethane → HCID 178511423, compound

HRID 2380367Notes

Reaction equation

HRID 2380367 reaction equation
[CH:1]1([CH2:13][CH2:14][CH2:15][C:16]([C:18]2[C:19](=[O:24])[S:20][CH2:21][C:22]=2[OH:23])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:25][CH2:26][C:27]([CH2:31][OH:32])([CH2:29][OH:30])[NH2:28].[K+].[Br-]>C(O)C.O>[NH2:28][C:27]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:26][OH:25].[CH:1]1([CH2:13][CH2:14][CH2:15][C:16]([C:18]2[C:19](=[O:24])[S:20][CH2:21][C:22]=2[OH:23])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 253877Potassium BromideHCID 178520549HCID 178520549, compound

Product 1

HCID 178511423HCID 178511423, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 0.8 g (2.3 mmol) of 3-(4-cyclododecyl-1-oxobutyl)-4-hydroxy-2-(5H)thiophenone in 20 mL of ethanol at 70° C. is added 0.26 g (2.2 mmol) of trishydroxymethyl aminomethane dissolved in 5 mL of water. The reaction mixture is stirred at 70° C. for 0.5 hours and then the solvents are evaporated. The residue is recrystallized from tetrahydrofuran/ether (2:1) to give 0.66 g of an off white solid: m.p. 141°-144° C.; IR (KBr) 3420, 2920, 2830, 1580 cm-1 ; NMR (DMSO-d6) δ1.11.-1.4 (m, 10H), 2.55 (t, J=7 Hz, 2H), 3.26 (s, 1H), 3.31 (s, 4H), 3.47 (d, J=5, 3 Hz), 5.15 (t, J=5 Hz, 2H), 7.6 (bs, 2H); MS (DCI) [M+H]+ 353. Anal. Calc' d. for C4H43NO6S: C 60.86; H 9.15; N, 2.96 Found: C, 60.91; H 9.16; N, 2.88

Workup

  1. customthe solvents are evaporated
  2. customThe residue is recrystallized from tetrahydrofuran/ether (2:1)
  3. customto give 0.66 g of an off white solid

Sources & evidence

ORD record
ord-aa4606097da249a1befbbe119da27ac5
Source dataset
uspto-grants-1994_11
Patent number
US05366993

Reaction notes

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