Benzoyl chloride, 3,4,5-trimethoxy- → HCID 18638174, compound

HRID 1165767Notes

Reaction equation

HRID 1165767 reaction equation
[OH:1][C@@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[N:4]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:3]1=[O:30])=[CH:21][CH:20]=[CH:19][CH:18]=3.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([O:44][CH3:45])[C:41]=1[O:42][CH3:43])[C:36](Cl)=[O:37]>N1C=CC=CC=1.CC(C)=O.C(Cl)Cl>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C@@H:8]2[S:7][C:6]3[C:17]4[C:22]([CH:23]=[CH:24][C:5]=3[N:4]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:3](=[O:30])[C@@H:2]2[O:1][C:36](=[O:37])[C:35]2[CH:34]=[C:33]([O:32][CH3:31])[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[CH:39]=2)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 13823438HCID 13823438, compound

Product 1

HCID 18638174HCID 18638174, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

To a solution of 1.50 g (0.0035 mol) of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b][1,4]thiazepin-4(5H)-one, in 20 ml of dry pyridine was added dropwise 1.4 g (0.0059 mol) of 3,4,5-trimethoxybenzoyl chloride at ice-bath temperature. The mixture was stirred at this temperature for 17 hours and concentrated to dryness. The residue was partitioned between methylene chloride and dilute ammonium hydroxide. The methylene chloride extracts were washed with brine and dried (MgSO4). Removal of the solvent gave a residue, which was dissolved in a mixture of acetone-methylene chloride (70:30) and chromatographed on 40 g silica gel. The column was eluted with 50 ml portions of acetone-methylene chloride (70:30). Fractions 4-15 were combined and the solvent was removed under reduced pressure to give 1.3 g of crude product, which after crystallization from ethanol afforded 1.2 g (55%) of (±)-cis-2,3-dihydro-2-(4-methoxyphenyl)-3 -[(3,4,5-trimethoxybenzoyl)oxy]-5-[2-(dimethylamino)ethyl]naphtho[1,2-b][1,4]thiazepin-4(5H)-one, mp 189°-190°.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between methylene chloride and dilute ammonium hydroxide
  3. washThe methylene chloride extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. customgave a residue, which
  7. customchromatographed on 40 g silica gel
  8. washThe column was eluted with 50 ml portions of acetone-methylene chloride (70:30)
  9. customthe solvent was removed under reduced pressure
  10. customto give 1.3 g of crude product, which
  11. customafter crystallization from ethanol

Sources & evidence

ORD record
ord-738d4897521643cf9bc333d603b02d8d
Source dataset
uspto-grants-1990_03
Patent number
US04912102

Reaction notes

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