Boron Trichloride → HCID 18461155, compound

HRID 2303379Notes

Reaction equation

HRID 2303379 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]3[CH:15]=[C:16]([O:19]C)[CH:17]=[CH:18][C:12]=3[C:11]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[C:25]([C:38]#[N:39])[CH:24]=2)=[O:22])=[CH:6][CH:5]=1.B(Cl)(Cl)[Cl:41]>ClC(Cl)C>[ClH:41].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:12]=3[C:11]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)=[C:25]([C:38]#[N:39])[CH:24]=2)=[O:22])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 18461151HCID 18461151, compound

Product 1

HCID 18461155HCID 18461155, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The title compound was prepared by dissolving 1.6 g (3.04 mmol) of [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]3-cyanophenyl]methanone hydrochloride in 20 mL of dichloroethane. 2.1 mL of condensed BCl3 was added and sealed in a vessel at room temperature. The reaction was allowed to proceed for sixteen hours. The reaction was quenched by pouring onto ice. The crude product was collected in the organic layer and evaporated to a solid. The product was further purified by chromatography and the hydrochloride prepared as in Preparation 1.

Workup

  1. additionwas added
  2. customsealed in a vessel at room temperature
  3. waitto proceed for sixteen hours
  4. customThe reaction was quenched
  5. additionby pouring onto ice
  6. customThe crude product was collected in the organic layer
  7. customevaporated to a solid
  8. customThe product was further purified by chromatography
  9. customthe hydrochloride prepared as in Preparation 1

Sources & evidence

ORD record
ord-81693ff66cef429aab20901cd71b8f10
Source dataset
uspto-grants-2002_08
Patent number
US06432982B1

Reaction notes

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