Phosphorus oxychloride → HCID 59854662, compound

HRID 2112769Notes

Reaction equation

HRID 2112769 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]([O:13]CC)=O.[CH2:16]([NH:23][C:24](=O)[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O=P(Cl)(Cl)Cl>ClCCCl>[CH2:16]([N:23]1[C:11](=[O:13])[C:3]2[C:4]3[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]=2[N:1]=[C:24]1[C:25]1[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylateHCID 7369623940-84-9

Product 1

HCID 59854662HCID 59854662, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Commercially available ethyl 2-amino-4,5,6,7-tetrahydrobenzo(b)-thiophene-3-carboxylate (6.0 g, 26.6 mmol, 100 mol-%) and N-benzyl-3,4,5-trimethoxybenzamide (10.4 g, 34.6 mmol, 130 mol-%) were dissolved in dry 1,2-dichloroethane. The reaction mixture was cooled with an ice-salt-bath and POCl3 (1.7 ml, 24.6 mmol, 130 mol-%) was added. The reaction mixture was refluxed for 24 hours. During refluxing POCl3 (340 μl) was added twice. The reaction mixture was poured into ice-water and after neutralization with sodium acetate the product was extracted into dichloromethane. The organic phases combined were washed with sodium bicarbonate sat. (3×50 ml) and dried with MgSO4. The yield after recrystallization from i-propanol was 8.3 g (yield 68%).

Workup

  1. temperatureThe reaction mixture was cooled with an ice-salt-bath
  2. temperatureThe reaction mixture was refluxed for 24 hours
  3. additionwas added twice
  4. extractionafter neutralization with sodium acetate the product was extracted into dichloromethane
  5. washThe organic phases combined were washed with sodium bicarbonate sat. (3×50 ml)
  6. dry with materialdried with MgSO4
  7. customThe yield
  8. customafter recrystallization from i-propanol

Sources & evidence

ORD record
ord-c07fc0817dbc477092bbf697253815a9
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

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