Chloroacetonitrile → HCID 18634526, compound

HRID 1486463Notes

Reaction equation

HRID 1486463 reaction equation
[Br-].[C:2]([O:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@H:7]1[S:25][C:26](N)=[NH2+])(=[O:4])[CH3:3].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].ClC[C:46]#[N:47]>CC(C)=O.O>[C:2]([O:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@H:7]1[S:25][CH2:26][C:46]#[N:47])(=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 656671Sodium PyrosulfiteHCID 8669893751224-13-6

Product 1

HCID 18634526HCID 18634526, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

2-S-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-2-thiouronium bromide (7; 16.11 g, 31.07 mmol), sodium metabisulphite (11.81 g, 62.14 mmol), potassium carbonate (4.72 g, 34.18 mmol), and chloroacetonitrile (8.21 g, 108.7 mmol) were dissolved in acetone/water (50:50 v/v, 200 mL), and stirred for 1 hour at room temperature. The reaction mixture was poured in ice-water (300 mL), and stirred for an additional 2 hours. The white precipitate was collected by filtration and recrystallized from hot methanol (30 mL). The product was filtered off as a white crystalline solid (9.61 g, 77%). M.p.=97° C. (Lit: 95-97° C.). 1H-NMR (400 MHz, CDCl3): δ=2.00 (s, 3H, CH3), 2.07 (s, 3H, CH3), 2.09 (s, 3H, CH3), 2.17 (s, 3H, CH3), 3.35 (d, J=17 Hz, 1H, S—CH), 3.64 (d, J=17 Hz, 1H, S—CH′), 4.01 (t, J=6.9 Hz, 1H, H5), 4.16 (m, 2H, H6, H6′), 4.7 (d, J1,2=10 Hz, 1H, H1), 5.11 (dd, J3,4=3.2 Hz, J2,3=10 Hz, 1H, H3), 5.24 (t, J=10 Hz, 1H, H2), 5.47 (d, J=2.4 Hz, 1H, H4). FT-IR (ATR): ν=2249 (CN, w), 1739 (C═O, s).

Workup

  1. stirringstirred for an additional 2 hours
  2. filtrationThe white precipitate was collected by filtration
  3. customrecrystallized from hot methanol (30 mL)
  4. filtrationThe product was filtered off as a white crystalline solid (9.61 g, 77%)
  5. customM.p.=97° C. (Lit: 95-97° C.)

Sources & evidence

ORD record
ord-69d8858b53d243319d01e7f3b2c59f32
Source dataset
uspto-grants-2016_08
Patent number
US09427482B2

Reaction notes

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