Dimethylformamide → HCID 57855419, compound

HRID 1516940Notes

Reaction equation

HRID 1516940 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[CH:10][C:11]([OH:13])=O)[CH2:7][CH2:8][CH2:9][C:2]1=2.CN(C=O)C.[CH3:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH2:21]([N:20]([CH3:19])[C:11](=[O:13])/[CH:10]=[C:6]1\[CH2:7][CH2:8][CH2:9][C:2]2[S:1][CH:5]=[CH:4][C:3]\1=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 53667594HCID 53667594, compound

Product 1

HCID 57855419HCID 57855419, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of a mixture E/Z of 2-(6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)acetic acid (0.38 g, 1.96 mmol) in thionyl chloride (3 mL) and a catalytic amount of DMF is refluxed for 5 min. The solvent is evaporated at reduced pressure and the residue is slowly added to a solution of N-methyl-N-benzylamine (0.24 g, 1.96 mmol) and triethylamine (0.5 mL) in dry CH2Cl2 (15 mL) cooled in an ice bath and stirred at room temperature monitoring the reaction by TLC. The solution is washed with water and the organic phase is dried and evaporated under reduced pressure, and the resulting crude is purified by column chromatography, giving (E)-N-benzyl-2-(6,7-dihydrobenzo[b]thien-4(5H)-ylidene)-N-methylacetamide (0.35 g, 1.17 mmol, 60%, viscous oil). 1H NMR (300 MHz, CDCl3): δ 1.95 (m, 2H), 2.87 (m, 4H), 3.00 (s, 3H), 4.65 (s, 2H), 6.34 (s, 1H), 7.04 (d, J=5.3 Hz, 1H), 7.09 (d, J=5.3 Hz, 1H), 7.23-7.38 (m, 5H).

Workup

  1. customThe solvent is evaporated at reduced pressure
  2. temperaturecooled in an ice bath
  3. customthe reaction by TLC
  4. washThe solution is washed with water
  5. customthe organic phase is dried
  6. customevaporated under reduced pressure
  7. customthe resulting crude is purified by column chromatography

Sources & evidence

ORD record
ord-cb90d5126a1c440ea30ea3d7fdd8487d
Source dataset
uspto-grants-2012_07
Patent number
US08227625B2

Reaction notes

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