Dichloromethane → HCID 70513155, compound

HRID 1263054Notes

Reaction equation

HRID 1263054 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12](Br)=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7](C3C=CC=CC=3)[C:6]=2[CH:22]=1.[NH:23]1[CH2:28][CH2:27][S:26][CH2:25][CH2:24]1.C(Cl)Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:23]4[CH2:28][CH:27]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:22]=5)[S:26][CH2:25][CH2:24]4)=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[CH:7][C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67164ThiomorpholineHCID 12246026HCID 12246026, compound

Product 1

HCID 70513155HCID 70513155, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2.0 gm (5.35 mmol) of 8-chloro-1-bromo-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine and 2.0 ml of thiomorpholine was heated under nitrogen in an oil bath at 120° C. for 18 hr and then allowed to cool. The reaction mixture was treated with methylene chloride and water. The organic layer was separated, washed with dilute brine and concentrated in vacuo. The residue was recrystallized from methanol to yield 1.40 gm (72.7%) with m.p. 241°-243° C. and 0.46 gm (23.9%) with m.p. 239°-241° C. of the title product. Analysis of the title product for carbon, hydrogen, nitrogen, chlorine and sulphur revealed 60.47% C, 4.58% H, 18.03% N, 9.14% Cl, and 8.09% S. Calculated values for such an analysis for the title product are: 60.67% C, 4.58% H, 17.69% N, 8.98% Cl, and 8.10% S.

Workup

  1. temperatureto cool
  2. customThe organic layer was separated
  3. washwashed with dilute brine
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-8eadc98859de40359095015cb9f461fe
Source dataset
uspto-grants-1984_06
Patent number
US04455307

Reaction notes

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