O-Xylene → 2H-1,5-Benzodiazepine-2-thione, 1,3-dihydro-4-phenyl-

HRID 1580551Notes

Reaction equation

HRID 1580551 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C1(C)C(C)=CC=CC=1.[C:17]([CH2:25][C:26](S)=[S:27])(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O1CCOCC1>O>[C:18]1([C:17]2[CH2:25][C:26](=[S:27])[NH:8][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[N:7]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 7243O-PhenylenediamineHCID 312751,4-DioxaneHCID 11138043HCID 11138043, compound

Product 1

HCID 30329842H-1,5-Benzodiazepine-2-thione, 1,3-dihydro-4-phenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.08 g of o-phenylendiamine, 10 ml of xylene and 1.96 g of benzoyldithioacetic acid (Thuillier et al - Bull. Soc. Chim. Fr. 1938 (1959) is refluxed for 1 hour under a stream of nitrogen. The reaction may also be carried out in water, alcohol or dioxane. After cooling, the precipitate is filtered, washed with ethyl ether, and crystallized from ethyl acetate. Yield 2 g, m.p. 228°-230°C.

Workup

  1. temperature1938 (1959) is refluxed for 1 hour under a stream of nitrogen
  2. customThe reaction
  3. temperatureAfter cooling
  4. filtrationthe precipitate is filtered
  5. washwashed with ethyl ether
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-578e21f2f5b84458b25b5a8d1fbdf87a
Source dataset
uspto-grants-1976_01
Patent number
US03933793

Reaction notes

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