Triethylamine → 4-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)thiomorpholine 1,1-dioxide

HRID 517758Notes

Reaction equation

HRID 517758 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:6]=[N:5][N:4]=1.[NH:18]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]1.C(N(CC)CC)C>C(#N)C>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([N:7]2[C:3]([CH2:2][N:18]3[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]3)=[N:4][N:5]=[N:6]2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6484228Thiomorpholine 1,1-dioxideHCID 80271755-(Chloromethyl)-1-(3-(trifluoromethyl)phenyl)-1H-tetrazole

Product 1

HCID 866918874-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole (300 mg, 1.14 mmol, commercially available from Otava, Kiev, Ukraine) in acetonitrile (4 mL) was added thiomorpholine 1,1-dioxide (309 mg, 2.29 mmol, Apollo Scientific, Stockport, UK) and triethylamine (0.175 mL, 1.26 mmol). The reaction mixture was heated at 120° C. for 20 minutes in a microwave reactor. The reaction mixture was cooled and then the solvent removed under vacuum. The residue was purified by MDAP. Fractions containing the desired product were combined and the solvent removed to yield a colourless gum. The product was partitioned between DCM (6 mL) and saturated aqueous NaHCO3 (3 mL) and the organic layer collected via a hydrophobic frit. The solvent was removed under a stream of argon to yield the title compound as a white solid (0.246 g)

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed under vacuum
  3. customThe residue was purified by MDAP
  4. additionFractions containing the desired product
  5. customthe solvent removed
  6. customto yield a colourless gum
  7. customThe product was partitioned between DCM (6 mL) and saturated aqueous NaHCO3 (3 mL)
  8. customthe organic layer collected via a hydrophobic frit
  9. customThe solvent was removed under a stream of argon

Sources & evidence

ORD record
ord-b745501620244f4dacae0234dde72c93
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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