Dichloromethane → HCID 53653455, compound

HRID 2379066Notes

Reaction equation

HRID 2379066 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, 2 H, C-1'), 4.63 t, 2 H, exchanges with D2O, 2×OH), 3.54-3.48 (m, 1 H, C-3'), PHACTS-PCS 3.43-3.25 (m, 4 H, 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-fef32df031ef40c4bdfdb94df2f85508
Source dataset
uspto-grants-1994_11
Patent number
US05360795

Reaction notes

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