Triphenylphosphine → HCID 86748160, compound

HRID 2226979Notes

Reaction equation

HRID 2226979 reaction equation
[Br:1][CH2:2][C:3]1[S:4][C:5]2[S:10][CH:9]=[C:8]([Cl:11])[C:6]=2[N:7]=1.[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[Br-:1].[Cl:11][C:8]1[C:6]2[N:7]=[C:3]([CH2:2][P+:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:4][C:5]=2[S:10][CH:9]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18963856HCID 18963856, compound

Product 1

HCID 86748160HCID 86748160, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 300 mg (1.1 mmol) of 2-(bromomethyl)-6-chlorothieno[3.2-d1]thiazole (from Step 3) and 650 mg (2.4 mmol) of triphenylphosphine in 5 ml of acetonitrile was stirred at r.t. for 4 h. The product was precipitated from the solution with Et2O, filtered and swished with Et2O to give 400 mg (70%) of the title product. 1H NMR (DMSO-d6) 7.95-7.73(m, 16H), 5.91(d, J=14 Hz, 2H).

Workup

  1. customThe product was precipitated from the solution with Et2O
  2. filtrationfiltered

Sources & evidence

ORD record
ord-592cb0fce9ad40e2a14fed452d04e0ea
Source dataset
uspto-grants-1994_09
Patent number
US05350760

Reaction notes

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