Sulfuric acid magnesium salt (1:1) → 7-(4-chlorobenzoyl)-5-(3-chlorophenyl)-1,5-dihydro-4,1-benzothiazepin-2(3H)-one

HRID 860793Notes

Reaction equation

HRID 860793 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[S:18][CH2:19][C:20](O)=[O:21].[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:20](=[O:21])[CH2:19][S:18][CH:17]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)[C:3]=3[CH:4]=2)=[O:16])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69020567[[[2-Amino-5-(4-chlorobenzoyl)phenyl](3-chlorophenyl)methyl]thio]-acetic acid

Product 1

HCID 690195197-(4-chlorobenzoyl)-5-(3-chlorophenyl)-1,5-dihydro-4,1-benzothiazepin-2(3H)-oneYield 4.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of intermediate (19) (0.079 mol) and MgSO4 (35.5 g) in toluene (500 ml) was stirred and refluxed overnight in a Dean-Stark apparatus and then cooled. The precipitate was filtered off and the filtrate was evaporated till dryness. The residue (35 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc 85/15; 20–45 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from acetonitrile and DIPE. The precipitate was filtered off and dried, yielding 1.5 g (4.4%) of 7-(4-chlorobenzoyl)-5-(3-chlorophenyl)-1,5-dihydro-4,1-benzothiazepin-2(3H)-one (intermediate 20), mp. 222° C.

Workup

  1. temperaturerefluxed overnight in a Dean-Stark apparatus
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate was evaporated till dryness
  5. customThe residue (35 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc 85/15; 20–45 μm)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from acetonitrile and DIPE
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-3a34b6d438d1495e9a8c3f4b1c0f89e4
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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