Hydrochloric Acid → 5-(3-chlorophenyl)-7-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

HRID 860785Notes

Reaction equation

HRID 860785 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[O:16][CH2:15][CH2:14][O:13]2)=[CH:8][C:7]=1[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)[OH:25])=[O:4].CC(O)(C)C.[K].Cl>COCCOC>[Cl:32][C:28]1[CH:27]=[C:26]([CH:24]2[C:7]3[CH:8]=[C:9]([C:12]4([C:17]5[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=5)[O:16][CH2:15][CH2:14][O:13]4)[CH:10]=[CH:11][C:6]=3[NH:5][C:3](=[O:4])[CH2:2][O:25]2)[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 5462222PotassiumHCID 690195152-bromo-N-[4-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-2-[(3-chlorophenyl)hydroxymethyl]phenyl]-acetamide

Product 1

HCID 690207365-(3-chlorophenyl)-7-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-1,5-dihydro-4,1-benzoxazepin-2(3H)-oneYield 51.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of intermediate (10) (0.072 mol) in DME (300 ml) was cooled on an ice bath. 2-methyl-2-propanol, potassium salt (0.144 mol) was added portionwise. The mixture was stirred at a low temperature for 30 min, at room temperature for 30 min, hydrolyzed and acidified with HCl. The precipitate was filtered off, rinced and dried, yielding 17 g (51.8%) of 5-(3-chlorophenyl)-7-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-1,5-dihydro-4,1-benzoxazepin-2(3H)-one (intermediate 11), mp. 205° C.

Workup

  1. temperaturewas cooled on an ice bath
  2. filtrationThe precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-f267ef298553477e8863df6584e8295c
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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