Dichloromethane → HCID 53653455, compound

HRID 727032Notes

Reaction equation

HRID 727032 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 D2 O, 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-aad7c40b5c1748de8980ce17ef28fb52
Source dataset
uspto-grants-1998_01
Patent number
US05712255

Reaction notes

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