Isopropylamine → HCID 68881870, compound

HRID 896693Notes

Reaction equation

HRID 896693 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[C:9](\[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)/[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[CH:34]([NH2:37])([CH3:36])[CH3:35].[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH:34]([NH:37][C:10](=[O:12])/[C:9](/[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)=[CH:8]/[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:36])[CH3:35]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 68881866HCID 68881866, compound

Product 1

HCID 68881870HCID 68881870, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of (E)-3-(3-bromophenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenoic acid from Step 1 (24.9 g, 65 mmol) in toluene (250 mL) was added thionyl chloride (14.3 mL, 196 mmol) and triethylamine (34 mL, 245 mmol). After stirring at 21° C. for 0.5 h., isopropyl amine (28 mL, 327 mmol) was added. After a further 2 h at r.t., the mixture was cooled to 0° C. and was neutralised with saturated NH4Cl solution, then extracted with EtOAc. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (Hex:EtOAc, 1:1 to pure EtOAc) yielded the (E)-N-isopropyl-3-(3-bromophenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenamide compound.

Workup

  1. waitAfter a further 2 h at r.t.
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed (H2O, brine)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (Hex:EtOAc, 1:1 to pure EtOAc)

Sources & evidence

ORD record
ord-486deb7e9e464d418c386479a3e7f40b
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

Loading…