Ammonia → Thiourea, beta-D-glucopyranosyl-

HRID 1163876Notes

Reaction equation

HRID 1163876 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[N:24]1C(=O)C(=CC2C=CC=CC=2)S[C:25]1=[S:37])(=O)C.[NH3:38]>CO>[C@@H:6]1([NH:24][C:25]([NH2:38])=[S:37])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54028629HCID 54028629, compound

Product 1

HCID 2728946Thiourea, beta-D-glucopyranosyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2,3,4,6-Tetra-O-acetyl-β-D glucopyranosyl)-5-benzylidenerhodanine(5.52 g., 0.01 mole) was added to a solution of 50 ml. of methanol saturated with ammonia at 0° in a pressure bottle. The mixture was stirred at room temperature for 18 hours with the stopper well closed. The mixture was evaporated to a syrupy material below 30° in vacuo. The residue was dissolved in the minimum amount of methanol and passed through a silica gel column(2.54×15 cm) with aid of additional methanol. One hundred ml. of effluent was collected and concentrated. During the concentration, a precipitate was formed. The white precipitate was filtered and dried at room temperature in vacuo, yielding 2.04 g. (86.8%); m.p. 207°-209°(dec.). (Lit. m.p. 207°-210°(83), m.p. 211°-212°(32), m.p. 205°-207°(86).

Workup

  1. customat 0°
  2. customwell closed
  3. customThe mixture was evaporated to a syrupy material below 30° in vacuo
  4. dissolutionThe residue was dissolved in the minimum amount of methanol
  5. customof effluent was collected
  6. concentrationconcentrated
  7. concentrationDuring the concentration
  8. customa precipitate was formed
  9. filtrationThe white precipitate was filtered
  10. customdried at room temperature in vacuo
  11. customyielding 2.04 g

Sources & evidence

ORD record
ord-b2782b6dbd9f4d47a990e9e18265d5bc
Source dataset
uspto-grants-1983_01
Patent number
US04367226

Reaction notes

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