Hydrazine hydrate (1:1) → 2-hydrazino-5-o-chlorophenyl-7-ethyl-3H-thieno[2,3-e][1,4]diazepine

HRID 1606040Notes

Reaction equation

HRID 1606040 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:10]=2[NH:11][C:12](=S)[CH2:13][N:14]=1.O.[NH2:22][NH2:23]>C(O)C>[NH:22]([C:12]1[CH2:13][N:14]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]2[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:10]=2[N:11]=1)[NH2:23]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135667575HCID 135667575, compound

Product 1

HCID 124342992-hydrazino-5-o-chlorophenyl-7-ethyl-3H-thieno[2,3-e][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[d] 32.1 g of 5-o-chlorophenyl-7-ethyl-1,2-dihydro-3H-thieno[2,3-e][1,4] diazepine-2-thione obtained in the above example [a] is suspended in 200 ml of ethanol, and to the suspension is added 8 g of hydrazine hydrate. Several minutes stirring turns the suspension into a homogeneous, red, transparent solution. Then crystals begin to precipitate. After stirring at room temperature for 2 hours and subsequent ice-cooling, the crystals are collected by suction filtration and washed well with methanol to give 28.6 g of almost pure 2-hydrazino-5-o-chlorophenyl-7-ethyl-3H-thieno[2,3-e][1,4]diazepine as yellowish crystals. The crystals, when recrystallized from a mixture of ethanol and diemethylformamide, show a melting point of 214° - 216°C (decomposition).

Workup

  1. customto precipitate
  2. stirringAfter stirring at room temperature for 2 hours
  3. temperaturesubsequent ice-cooling
  4. filtrationthe crystals are collected by suction filtration
  5. washwashed well with methanol

Sources & evidence

ORD record
ord-f54d369660fb42fe87d1e28533c55c95
Source dataset
uspto-grants-1976_04
Patent number
US03952006

Reaction notes

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