Hydrazine hydrate (1:1) → HCID 66768172, compound

HRID 57280Notes

Reaction equation

HRID 57280 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:13]1[CH2:17][CH2:16][CH2:15][O:14]1)[C:11]#[N:12].O.[NH2:19][NH2:20]>C(O)C>[NH2:12][C:11]1[C:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[C:13]([CH2:17][CH2:16][CH2:15][OH:14])[NH:19][N:20]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66768211Benzothiazol-2-yl-(dihydrofuran-2-ylidene)-acetonitrile

Product 1

HCID 66768172HCID 66768172, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The benzothiazol-2-yl-(dihydrofuran-2-ylidene)-acetonitrile (90 mg, 0.37 mmol) prepared above and hydrazine hydrate (25 mg, 0.5 mmol) were refluxed in ethanol (15 mL) for 10 hours. The solvent was evaporated and the resulting residue was triturated with dichloromethane. The solid was isolated by filtration and was then washed with dichloromethane and methanol to yield 60 mg (67%) of the title compound as a cream coloured solid. MS (m/z, ES+): 275.1 (M+1, 100). 1H NMR (300 MHz, ppm, DMSO-d6): δ (ppm), 11.5-12.2 (br s, 1H), 8.00 (d, 1H), 7.86 (d, 1H), 7.77 (t, 2H), 7.29 (t, 1H), 7.00-5.20 (br m, 2H), 4.55 (s, 1H), 3.52 (q, 2H), 2.83 (br s, 2H), 1.84 (q, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting residue was triturated with dichloromethane
  3. customThe solid was isolated by filtration
  4. washwas then washed with dichloromethane and methanol

Sources & evidence

ORD record
ord-a6135fe8fa514a139199882f2b635744
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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