Sulfuric Acid → 4-O-Hexopyranosyl-N-[hydroxy(imino)methyl]hexopyranosylamine

HRID 2286677Notes

Reaction equation

HRID 2286677 reaction equation
O.O[CH:3]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:8]([O:9][C@@H:10]2[O:18][C@H:17]([CH2:19][OH:20])[C@H:15]([OH:16])[C@H:13]([OH:14])[C@H:11]2[OH:12])[C@H:6]([OH:7])[C@H:4]1[OH:5].[NH2:25][C:26]([NH2:28])=[O:27].OS(O)(=O)=O>O>[CH2:19]([OH:20])[C@H:17]1[O:18][C@@H:10]([O:9][C@H:8]2[C@H:6]([OH:7])[C@@H:4]([OH:5])[CH:3]([NH:25][C:26]([NH2:28])=[O:27])[O:22][C@@H:21]2[CH2:23][OH:24])[C@H:11]([OH:12])[C@@H:13]([OH:14])[C@H:15]1[OH:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1176UreaHCID 62223Lactose monohydrate

Product 1

HCID 1935994-O-Hexopyranosyl-N-[hydroxy(imino)methyl]hexopyranosylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

360 g of lactose monohydrate (1 mole) were mixed with 60 g of urea (1 mole) and 10.6 ml of a solution made up of 100 ml of H2O and 6 ml of 98% H2SO4. The mixture was melted and deposited as a thin layer on the moving belt of a tunnel oven. This oven was equipped with a system for controlling its temperature in a first third of its length (zone I) according to a temperature gradient and, in the second 2/3 of its length (zone II), at a constant temperature. Zone I was subjected to a temperature gradient ranging from ambient, at the entrance, to 100°-110° at the end of zone I; zone II was maintained at a constant temperature of 100°-110° C. The mixture coated on the belt thus penetrated into the tunnel and was gradually heated, in 11/2 hrs, to 110° after which it entered zone II where it stayed for 2-3 hrs at 110° C. At the exit of the tunnel, the mixture was cooled and had the aspect of a slightly foamy, crystalline, light brown material, easy to remove from the belt with a doctor-knife and which could be ground into a powder. This product was collected in a continuous manner and about 400 g were obtained.

Workup

  1. customdeposited as a thin layer on the moving belt of a tunnel oven
  2. customThis oven was equipped with a system
  3. customto 100°-110°
  4. temperaturewas gradually heated, in 11/2 hrs
  5. customto 110°
  6. temperatureAt the exit of the tunnel, the mixture was cooled
  7. customeasy to remove from the belt with a doctor-knife and which
  8. customThis product was collected in a continuous manner
  9. customabout 400 g were obtained

Sources & evidence

ORD record
ord-cd6c6a45db5e427e981f565f4f8efd0b
Source dataset
uspto-grants-1981_05
Patent number
US04267314

Reaction notes

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