Methanol → HCID 53734506, compound

HRID 2051837Notes

Reaction equation

HRID 2051837 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH2:19][CH2:20][CH2:21][CH3:22])[CH:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@@H:9]1[OH:10])=[O:6].[N:23]([O-])=[O:24].[Na+].CO.C(=O)([O-])[O-].[K+].[K+]>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:23]=[O:24])[C:5]([N:7]([CH2:19][CH2:20][CH2:21][CH3:22])[CH:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@@H:9]1[OH:10])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 53937510HCID 53937510, compound

Product 1

HCID 53734506HCID 53734506, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

5.4 g of 1-(2-chloroethyl)-3-n-butyl-3-D-mannopyranosylurea are dissolved in 20 ml of formic acid, and 3.5 g of sodium nitrite are added gradually thereto for 2 hours under ice-cooling and stirring. 40 ml of methanol and 30 g of potassium carbonate anhydrate are added to said mixture. Then, said mixture is further stirred for 10 minutes under ice-cooling. After the reaction, the mixture is treated in the same manner as described in Example 5-(2). 1.6 g of 1-(2-chloroethyl)-1-nitroso-3-n-butyl-3-D-mannopyranosylurea are thereby obtained as yellow caramel.

Workup

  1. temperaturefor 2 hours under ice-cooling
  2. stirringis further stirred for 10 minutes under ice-
  3. temperaturecooling
  4. customAfter the reaction
  5. additionthe mixture is treated in the same manner

Sources & evidence

ORD record
ord-f47593b0125a4d069e594b3f39a556d0
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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