Dimethylamine → 7-Chloro-2-[2-(dimethylamino)ethyl]-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione oxalate hydrate

HRID 1194225Notes

Reaction equation

HRID 1194225 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][CH2:13]Cl)[CH2:9][N:8]([CH3:15])[C:7](=[S:16])[C:6]=2[CH:17]=1.[CH3:18][NH:19][CH3:20].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23]>C(O)C.C(O)(C)C>[OH2:11].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][CH2:13][N:19]([CH3:20])[CH3:18])[CH2:9][N:8]([CH3:15])[C:7](=[S:16])[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 971Oxalic AcidHCID 137263017-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione

Product 1

HCID 137263387-Chloro-2-[2-(dimethylamino)ethyl]-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione oxalate hydrate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 8.0 g (0.027 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione in 50 ml of absolute ethanol was added 6 ml (0.054 mole) of 40% aqueous solution of dimethylamine. The solution was heated in a steel bomb at 90° C. for 14 hr. The ethanol was removed under reduced pressure and the residue was partitioned between chloroform and aqueous sodium hydroxide. The chloroform layer was concentrated to give a viscous yellow oil. The oil was dissolved in isopropyl alcohol and reacted with oxalic acid. The oxalate salt immediately precipitated. The mixture was heated and a small amount of water was added to dissolve the salt. A white crystalline powder was obtained, m.p. 150°-151° C.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. customthe residue was partitioned between chloroform and aqueous sodium hydroxide
  3. concentrationThe chloroform layer was concentrated
  4. customto give a viscous yellow oil
  5. customThe oxalate salt immediately precipitated
  6. temperatureThe mixture was heated
  7. additiona small amount of water was added
  8. dissolutionto dissolve the salt
  9. customA white crystalline powder was obtained

Sources & evidence

ORD record
ord-3ac89584dd6142e5a3d030b5bd75a1ef
Source dataset
uspto-grants-1989_03
Patent number
US04812565

Reaction notes

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