2-Propanol, reaction products with ammonia, distn. residues → HCID 10279755, compound

HRID 860808Notes

Reaction equation

HRID 860808 reaction equation
[NH3:1].CC(O)C.Cl[C:7]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)([C:28]1[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=1)[C:8]1[CH:9]=[CH:10][C:11]2[N:17]([CH3:18])[C:16](=[O:19])[CH2:15][S:14][CH:13]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:12]=2[CH:27]=1>C1COCC1>[NH2:1][C:7]([C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)([C:28]1[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=1)[C:8]1[CH:9]=[CH:10][C:11]2[N:17]([CH3:18])[C:16](=[O:19])[CH2:15][S:14][CH:13]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:12]=2[CH:27]=1

Participants

4

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 690229887-[chloro(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-5-(3-chlorophenyl)-1,5-dihydro-1-methyl-4,1-benzothiazepin-2(3H)-one

Product 1

HCID 10279755HCID 10279755, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

NH3/2-propanol (10 ml) was added dropwise at 5° C. under N2 flow to a mixture of 7-[chloro(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-5-(3-chlorophenyl)-1,5-dihydro-1-methyl-4,1-benzothiazepin-2(3H)-one (described in Example B11a) (0.00247 mol) in THF (15 ml). The mixture was stirred at 5° C. for 1 hour and at room temperature for 2 hours, then poured out into ice water and extracted with CH2Cl2. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue (1.2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.5; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.35 g, 27%). was crystallized from acetonitrile and diethyl ether. The precipitate was filtered off and dried in vacuo, yielding 0.28 g (22%) of 7-[amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-5-(3-chlorophenyl)-1,5-dihydro-1-methyl-4,1-benzothiazepin-2(3H)-one, mp. 218° C.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (1.2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.5; 15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customwas crystallized from acetonitrile and diethyl ether
  11. filtrationThe precipitate was filtered off
  12. customdried in vacuo

Sources & evidence

ORD record
ord-b4c595aea6884d01b310fcdc7d38a48d
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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