Dichloromethane → HCID 86591158, compound

HRID 860786Notes

Reaction equation

HRID 860786 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]3[NH:17][C:16](=O)[CH2:15][N:14]=[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[C:12]=3[CH:26]=2)=[O:7])=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30].C(Cl)Cl>C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]3[NH:17][C:16](=[S:30])[CH2:15][N:14]=[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[C:12]=3[CH:26]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14817Phosphorus sulfide (P2S5)HCID 69018742HCID 69018742, compound

Product 1

HCID 86591158HCID 86591158, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of intermediate (6) (0.01 mol) and tetraphosphorus decasulfide (0.012 mol) in THF (100 ml) was stirred at 60° C. for 6 hours, poured out into ice water and stirred for 1 hour. DCM was added. The mixture was stirred for 30 min, filtered over celite and washed several times with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (2.85 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 100%; 35–70 μm). The pure fractions were collected and the solvent was evaporated. The residue (1.3 g, 30.5%) was crystallized from acetonitrile. The precipitate was filtered off and dried, yielding 1.1 g (26%) of (4-chlorophenyl)[5-(3-chlorophenyl)-2,3-dihydro-2-thioxo-1H-1,4-benzodiazepin-7-yl]-methanone (intermediate 13), mp. 125° C.

Workup

  1. stirringstirred for 1 hour
  2. stirringThe mixture was stirred for 30 min
  3. filtrationfiltered over celite
  4. washwashed several times with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated till dryness
  9. customThe residue (2.85 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 100%; 35–70 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue (1.3 g, 30.5%) was crystallized from acetonitrile
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-2dba9a99b27c464ebbde9065e10a723d
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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