Acetic Acid → HCID 90412576, compound

HRID 924282Notes

Reaction equation

HRID 924282 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([NH:12][NH2:13])=[S:11])[CH3:2].C(O)(=O)C.[N:18]([O-])=O.[Na+]>O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[S:11][N:18]=[N:13][N:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2758894N-(2-Ethylphenyl)hydrazinecarbothioamideHCID 23668193Sodium Nitrite

Product 1

HCID 90412576HCID 90412576, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled mixture of N-(2-ethylphenyl)hydrazinecarbothioamide (0.500 g, 2.56 mmol) and acetic acid (2.00 mL, 17.5 mmol) was added sodium nitrite (0.177 g, 2.56 mmol) in water (1 mL). The mixture turned yellow upon addition and the reaction was stirred for 1 hour. The solid was filtered and the title compound was obtained as an orange solid (0.389 g, 73%): 1H NMR (400 MHz, CDCl3) δ 9.02 (s, 1H), 7.42-7.28 (m, 4H), 2.76 (q, J=7.5 Hz, 2H), 1.25 (t, J=7.5 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 138.69, 137.90, 130.38, 128.28, 128.14, 121.60, 24.73, 14.79; ESIMS m/z 179 ([M+H]−N2+).

Workup

  1. temperaturecooled
  2. additionThe mixture turned yellow upon addition
  3. stirringthe reaction was stirred for 1 hour
  4. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-74ab5f12d85041b580992298995d0f5f
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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