Dichloromethane → HCID 131714707, compound

HRID 1981669Notes

Reaction equation

HRID 1981669 reaction equation
[N:1]([N+]([O-])=O)=[O:2].[CH2:6]([N:11]([CH:18]([OH:33])[C@H:19]1[O:25][C@:23]([CH2:26][CH2:27][CH2:28][CH3:29])([OH:24])[C@H:22]([OH:30])[C@@H:21]([OH:31])[C@@H:20]1[OH:32])[C:12](=[O:17])[NH:13][CH2:14][CH2:15][Cl:16])[CH2:7][CH:8]([CH3:10])[CH3:9].ClCCl.ClC1C=CC=CC=1>ClC(Cl)C>[CH2:6]([N:11]([CH:18]([OH:33])[C@H:19]1[O:25][C@:23]([CH2:26][CH2:27][CH2:28][CH3:29])([OH:24])[C@H:22]([OH:30])[C@@H:21]([OH:31])[C@@H:20]1[OH:32])[C:12](=[O:17])[N:13]([CH2:14][CH2:15][Cl:16])[N:1]=[O:2])[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7964ChlorobenzeneHCID 61526Nitrogen trioxideHCID 131714708HCID 131714708, compound

Product 1

HCID 131714707HCID 131714707, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dinitrogen trioxide gas (1.5 g) was introduced into a solution of the thus prepared 3-isopentyl-3-(n-butyl-α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (4.68 g, 11.38 mmol) in a mixture of dichloroethane (50 ml), dichloromethane (10 ml), and monochlorobenzene (10 ml) with thorough stirring at 10°-18° C., and stirring was continued for further one hour at the same temperature. The reaction mixture was vacuum-concentrated at 28° C. or below and purified by column chromatography (packing silica gel; eluent: octane/isopropyl acetate 4:1) to obtain 3-isopentyl-3-(n-butyl-α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea (3.82 g, 8.68 mmol); yield 76.3%; m.p. 66°-68° C.; [α]D20 +65.3° (C 1.0, methanol).

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture was vacuum-concentrated at 28° C. or below
  3. custompurified by column chromatography (packing silica gel; eluent: octane/isopropyl acetate 4:1)

Sources & evidence

ORD record
ord-b624738234ee4c278fe7bf9c3da60d59
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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