Tetrahydrofuran → HCID 53871027, compound

HRID 1419709Notes

Reaction equation

HRID 1419709 reaction equation
C[Mg]Cl.O1CCC[CH2:5]1.Cl[C:10]1[S:11][C:12]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([Cl:20])[C:13]=2[N:14]=1.[Cl-].[NH4+]>C(OCC)C.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:20][C:15]1[C:13]2[N:14]=[C:10]([CH3:5])[S:11][C:12]=2[CH:18]=[C:17]([F:19])[CH:16]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 534405702,4-Dichloro-6-fluoro-1,3-benzothiazoleHCID 178418332HCID 178418332, compound

Product 1

HCID 53871027HCID 53871027, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

67 ml of a solution of methyl magnesium chloride in tetrahydrofuran (3M; 0.2 mol) were added dropwise to a solution of 22 g (0.1 mol) of 2,4-dichloro-6-fluorobenzothiazole and 3.3 g (5 mmol) of dichlorobis(triphenylphosphine)nickel in 100 ml of diethyl ether. After stirring had been carried out for 2 hours, the mixture was poured onto saturated aqueous ammonium chloride solution. The desired product was extracted with diethyl ether, after which the combined organic phases were washed with water, dried over magnesium sulfate and finally evaporated down. 10 g of the desired product were obtained by crystallization from petroleum ether.

Workup

  1. extractionThe desired product was extracted with diethyl ether
  2. washafter which the combined organic phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customfinally evaporated down

Sources & evidence

ORD record
ord-82e7a942b1ef455fb8614a838e5d0e60
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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