Dichloromethane → HCID 53653455, compound

HRID 2289474Notes

Reaction equation

HRID 2289474 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][O:8][CH:9]([CH2:19][O:20]CC2C=CC=CC=2)[CH2:10][O:11]CC2C=CC=CC=2)[C:5]2[C:28]([Cl:35])=[C:29]([Cl:34])[C:30]([Cl:33])=[C:31]([Cl:32])[C:4]=2[N:3]=1.B(Cl)(Cl)Cl.C(Cl)Cl>CO>[Cl:1][C:2]1[N:6]([CH2:7][O:8][CH:9]([CH2:19][OH:20])[CH2:10][OH:11])[C:5]2[C:28]([Cl:35])=[C:29]([Cl:34])[C:30]([Cl:33])=[C:31]([Cl:32])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 54026302HCID 54026302, compound

Product 1

HCID 53653455HCID 53653455, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 155 (0.52 g, 51%) was prepared from 154 (1.5 g, 2.6 mmole), BCl3 (5M solution in CH2Cl2, 14 mL), CH2Cl2 (30 mL) and MeOH (20 mL) by the method described for 166 which on recrystallization from EtOAC gave 155: m.p. 155°; 1H NMR (DMSO-d6): d 5.76 (s, 2H, C-1'), 4.63 (t, 2H, exchanges with D2O, 2×OH), 3.54-3.48 (m, 1H, C-3'), 3.43-3.25 (m, 4H, C-4' and 5'H). Anal. Calcd. for C11H9N2Cl5O3 : C, 33.46; H, 2.28; N, 7.09. Found: C, 33.60; H, 2.15; N, 6.91.

Workup

  1. customdescribed for 166 which on recrystallization from EtOAC
  2. customgave 155

Sources & evidence

ORD record
ord-55c0385a11d64874ac7cb80afae4ebb8
Source dataset
uspto-grants-2000_07
Patent number
US06093698

Reaction notes

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