Ammonia → HCID 57991878, compound

HRID 2075356Notes

Reaction equation

HRID 2075356 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([NH:13][NH:14][C:15]([NH2:17])=[S:16])=O)[C:5]=2[CH:4]=[N:3][N:2]=1.S(=O)(=O)(O)O.N>>[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[S:16][C:15]([NH2:17])=[N:14][N:13]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][N:2]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 1118Sulfuric AcidHCID 57991941HCID 57991941, compound

Product 1

HCID 57991878HCID 57991878, compound

Procedure

To a 100 mL round bottom flask was added 1-(phthalazine-5-carbonyl)thiosemicarbazide (0.20 g, 0.81 mmol) and concentrated sulfuric acid (10 mL). The resulting solution was stirred at room temperature for 3 hours. The reaction mixture was poured into a mixture of 10 mL 33% aqueous ammonia and 10 mL ice with stirring. The resulting solution was adjusted to pH 8 with additional ammonia solution. The product was obtained as a yellow solid via filtration and washing with water. The solid was dried in a vacuum oven for 24 hours at 50° C. to provide 5-(phthalazine-5yl)-1,3,4-thiadiazol-2-amine. LCMS (M+H) 230.1 calc. C10H8N5S for 230.0. 1H NMR (400 MHz, CDCl3): δ ppm 8.23 (m, J=8.41 Hz, 1H) 8.46 (d, 1H) 8.53 (d, 1H) 9.63 (d, J=16.24 Hz, 2H). NH2 not detected.

Workup

  1. stirringwith stirring
  2. customThe product was obtained as a yellow solid via filtration
  3. washwashing with water
  4. customThe solid was dried in a vacuum oven for 24 hours at 50° C.

Sources & evidence

ORD record
ord-f1aec10162164c2b9321b1649540dab1
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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