Sulfuric acid magnesium salt (1:1) → HCID 10118352, compound

HRID 860802Notes

Reaction equation

HRID 860802 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([OH:16])[C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)=[CH:5][C:4]=1[CH:24]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)[S:25][CH2:26][C:27](O)=[O:28].[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[Cl:36][C:32]1[CH:31]=[C:30]([CH:24]2[C:4]3[CH:5]=[C:6]([C:9]([C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=4)([OH:16])[C:10]4[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=4)[CH:7]=[CH:8][C:3]=3[NH:2][C:27](=[O:28])[CH2:26][S:25]2)[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69020319HCID 69020319, compound

Product 1

HCID 10118352HCID 10118352, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of intermediate (3) (0.0103 mol) and MgSO4 (6.2 g) in toluene (155 ml) was stirred and refluxed for 5 hours, then filtered and washed with CH2Cl2/CH3OH 1/2. The organic layer was separated, washed with K2CO3 10%, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (3.35 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanone and diethyl ether. The precipitate was filtered off and dried, yielding 1.6 g (30%) of 5-(3-chlorophenyl)-7-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1,5-dihydro-4,1-benzothiazepin-2(3H)-one, mp. 210° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. filtrationfiltered
  3. washwashed with CH2Cl2/CH3OH 1/2
  4. customThe organic layer was separated
  5. washwashed with K2CO3 10%
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated till dryness
  9. customThe residue (3.35 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1; 15–40 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from 2-propanone and diethyl ether
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-fbbbcce848ff45d88dbb2b683a478c64
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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