Methylamine → HCID 178482322, compound

HRID 1763238Notes

Reaction equation

HRID 1763238 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7](=O)[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.O1CCCC1.[CH3:26][NH2:27]>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:27][CH3:26])[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 89657Desmethylclobazam

Product 1

HCID 178482322HCID 178482322, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

A suspension of 14.3g (0.05 mol) of 7-chloro-5-phenyl-1,2,3,5-tetrahydro-4H-1,5-benzodiazepin-2,4-dione in 1l of tetrahydrofuran and 200 ml of benzene was saturated with methylamine. A solution of 11.5 g (0.06 mol) of titanium tetrachloride in 200 ml of benzene was added at 0° through a dropping funnel. After stirring at 0° to 10° for 15 min, the mixture was heated to reflux for 1 1/2 hrs. It was then partitioned between water and benzene. The benzene layer was separated, dried and evaporated. Crystallization of the residue form methylene chloride/hexane yielded the above-named product, mp 215°-217°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 1/2 hrs
  3. customIt was then partitioned between water and benzene
  4. customThe benzene layer was separated
  5. customdried
  6. customevaporated
  7. customCrystallization of the residue form methylene chloride/hexane
  8. customyielded the above-named product, mp 215°-217°

Sources & evidence

ORD record
ord-6890582f3588413396e2d9a0c4c6a241
Source dataset
uspto-grants-1978_09
Patent number
US04111934

Reaction notes

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