Heptane → HCID 59520509, compound

HRID 1162784Notes

Reaction equation

HRID 1162784 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl:21][CH2:22][CH2:23][C:24](Cl)=[O:25].CCCCCCC>C1COCC1>[Cl:21][CH2:22][CH2:23][C:24]([NH:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:13][CH3:14])=[O:12])=[O:25]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 693643-Chloropropionyl chlorideHCID 36564302-amino-N-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

Product 1

HCID 59520509HCID 59520509, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (2.82 g, 13.41 mmol) was completely dissolved in THF (90 mL). Potassium carbonate (2.22 g, 16.09 mmol) was then added and the reaction stirred for 5 min. 3-chloropropanoyl chloride (2.04 g, 1.536 mL, 16.09 mmol) was added and the reaction mixture stirred at RT for 30 min. THF was removed in vacuo. Water was added and the reaction mixture extracted into EtOAc (×3). The combined EtOAc layers were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. Purification by flash column chromatography-silica gel and elution with 0-60% EtOAc:heptane gave the desired product (1.76 g, 5.87 mmol, 44%).

Workup

  1. stirringthe reaction mixture stirred at RT for 30 min
  2. customTHF was removed in vacuo
  3. additionWater was added
  4. extractionthe reaction mixture extracted into EtOAc (×3)
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customPurification
  10. washby flash column chromatography-silica gel and elution with 0-60% EtOAc

Sources & evidence

ORD record
ord-36a7562f09bd426d96dfbe29ddeca943
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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