4-Nitrobenzoyl chloride → 2-(4-Nitrophenyl)Benzo[D]Thiazole

HRID 2264110Notes

Reaction equation

HRID 2264110 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]2[S:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 87132-Aminothiophenol

Product 1

HCID 8275002-(4-Nitrophenyl)Benzo[D]ThiazoleYield 73.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-nitrobenzoyl chloride (1.49 g, 8.0 mmol) in benzene (anhydrous, 10 mL) was added dropwise to 2-aminothiophenol (1.0 g, 8.0 mmol in 10 ml of benzene) at room temperature. The reaction mixture was allowed to stir for 16 hr. The reaction was quenched with water (20 mL). The aqueous layer was separated and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried and evaporated. The crude product was purified with flush column, (hexane:ethyl acetate=85:15) to give 1.5 g (73.2%) of product as light yellow solid.

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. customThe combined organic layers were dried
  5. customevaporated
  6. customThe crude product was purified
  7. customwith flush column, (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-1ce233ea3ffd41108572060eabe8dda0
Source dataset
uspto-grants-2010_12
Patent number
US07854920B2

Reaction notes

Loading…