Ethane, 2-bromo-1,1-diethoxy- → HCID 118324018, compound

HRID 1778280Notes

Reaction equation

HRID 1778280 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:9](=[S:11])[NH2:10])=[CH:4][CH:3]=1.[CH2:21](OC(OCC)CBr)[CH3:22]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:9]2[S:11][CH:21]=[CH:22][N:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 118324019HCID 118324019, compound

Product 1

HCID 118324018HCID 118324018, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 2-(4-chlorophenyl)-2-(4-nitrophenyl)ethanethioamide (800 mg, 2.608 mmol, 1 equip) and bromoacetaldehyde diethyl acetal (2.055 g, 10.431 mmol, 4 equip) in acetic acid (12.09 mL) and water (0.47 mL) was heated at 100° C. for 45 minutes. The reaction mixture was poured into water and extracted with ethyl acetate (3×). The combined organic extracts were washed with water, saturated sodium bicarbonate, and then dried over Na2SO4, filtered, and concentrated. The residue was purified by MPLC using ethyl acetate-heptane as eluent to yield 2-((4-chlorophenyl)(4-nitrophenyl)methyl)thiazole as a viscous brown oil.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with water, saturated sodium bicarbonate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-9ef6c07edf1e4faea18dcb0904903bfc
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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