Ammonium Chloride → HCID 54423244, compound

HRID 1419719Notes

Reaction equation

HRID 1419719 reaction equation
[CH2:1]([Mg]Br)[CH3:2].Cl[C:6]1[S:7][C:8]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([Cl:16])[C:9]=2[N:10]=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:16][C:11]1[C:9]2[N:10]=[C:6]([CH2:1][CH3:2])[S:7][C:8]=2[CH:14]=[C:13]([F:15])[CH:12]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 534405702,4-Dichloro-6-fluoro-1,3-benzothiazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 54423244HCID 54423244, compound

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.2 mol of ethyl magnesium bromide in diethyl ether was added to a solution of 22.0 g (0.1 mol) of 2,4-dichloro-6-fluorobenzothiazole and 3.3 g (5 mmol) of dichlorobis(triphenylphosphine)nickel in 0.5 1 of diethyl ether. Stirring was carried out for 2 hours, after which the mixture was poured onto saturated aqueous ammonium chloride solution. The product was extracted with diethyl ether. The combined organic phases were washed with water, dried over magnesium sulfate and finally evaporated down. Purification of the crude product was effected by means of silica gel chromatography (eluent: 8:2 cyclohexane/methyl tert-butyl ether). Yield: 10.3 g.

Workup

  1. extractionThe product was extracted with diethyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customfinally evaporated down
  5. customPurification of the crude product

Sources & evidence

ORD record
ord-5e948661f41d4c2c87f97919c63db590
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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