Thiourea → 51224-13-6

HRID 1486462Notes

Reaction equation

HRID 1486462 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[Br:24])(=[O:3])[CH3:2].[NH2:25][C:26]([NH2:28])=[S:27]>CC(C)=O>[Br-:24].[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[S:27][C:26]([NH2:28])=[NH2+:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 2734143alpha-Acetobromogalactose

Product 1

HCID 8669893751224-13-6Yield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (6; 15.00 g, 36.48 mmol) and thiourea (3.05 g, 40.07 mmol) were dissolved in acetone (75 mL). The solution was heated to reflux for 2 hours, and subsequently filtered and cooled to 20° C. Addition of pentane (75 mL) resulted in the precipitation of the product as a white, crystalline solid (16.11 g, 91%). 1H-NMR (400 MHz, [D6]DMSO,): δ=1.95 (s, 3H, CH3), 2.01 (s, 3H, CH3), 2.08 (s, 3H, CH3), 2.14 (s, 3H, CH3), 4.09 (m, 2H, H6, H6′), 4.45 (t, J=6.4 Hz, 1H, H5), 5.11 (t, J2,3=10 Hz, 1H, H2), 5.22 (dd, J2,3=9.9 Hz, J3,4=3.2 Hz, 1H, H3), 5.39 (d, J=3.2 Hz, 1H, H4), 5.71 (d, J1,2=10 Hz, 1H, H1), 9.11 (br, 2H, NH2), 9.35 (br, 2H, NH2).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 hours
  3. filtrationsubsequently filtered
  4. additionAddition of pentane (75 mL)

Sources & evidence

ORD record
ord-e453abe8ac3542b4985ced8e04094371
Source dataset
uspto-grants-2016_08
Patent number
US09427482B2

Reaction notes

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