Triethylamine → HCID 70380960, compound

HRID 1247985Notes

Reaction equation

HRID 1247985 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[S:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([N+:44]([O-:46])=[O:45])=[C:39]([CH:43]=1)[C:40](Cl)=[O:41]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:40](=[O:41])[C:39]3[CH:43]=[C:35]([Cl:34])[CH:36]=[CH:37][C:38]=3[N+:44]([O-:46])=[O:45])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 91638DeacetyldiltiazemHCID 27236855-Chloro-2-nitrobenzoyl chloride

Product 1

HCID 70380960HCID 70380960, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.86 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 1 ml of triethylamine are dissolved in 15 ml of methylene chloride, and 1.27 g of 5-chloro-2-nitrobenzoyl chloride are added thereto. The mixture is stirred at room temperature for one hour. After the reaction, the mixture is poured into ice-water and then extracted with ethyl acetate. The extract is washed with an aqueous sodium bicarbonate solution, water and an aqueous sodium chloride solution, successively. Then, the extract is evaporated to remove solvent, and the residue is crystallized with ethanol. 2.45 g of (+)-cis-2-(4-methoxyphenyl)-3-(5-chloro-2-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as colorless prisms. Yield: 88.1%.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium bicarbonate solution, water
  4. customThen, the extract is evaporated
  5. customto remove solvent
  6. customthe residue is crystallized with ethanol

Sources & evidence

ORD record
ord-f272fb7802074de196ab0164600e1202
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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