Isopropyl Isothiocyanate → HCID 86725121, compound

HRID 634334Notes

Reaction equation

HRID 634334 reaction equation
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([NH:15][NH2:16])=[O:14])[CH:11]=2)[NH:6][CH:5]=1)([O-:3])=[O:2].[CH:17]([N:20]=[C:21]=[S:22])([CH3:19])[CH3:18]>CN(C=O)C>[CH:17]([NH:20][C:21]([NH:16][NH:15][C:13]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[N+:1]([O-:3])=[O:2])=[O:14])=[S:22])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 75263Isopropyl IsothiocyanateHCID 68328191HCID 68328191, compound

Product 1

HCID 86725121HCID 86725121, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-nitro-1H-indole-5-carbohydrazide (1.2 g, 5.454 mmol) in DMF (5 mL) was added isopropyl isothiocyanate (661 mg, 6.545 mmol) in one lot and the reaction was heated to reflux for 4 h. The mixture was quenched with water (20 mL) to get a pale yellow precipitate. The precipitate was filtered, washed with water (2×10 mL) and dried. The crude product was treated with 20% EtOAc in petroleum ether (2×20 mL) to afford N-isopropyl-2-(3-nitro-1H-indole-5-carbonyl)hydrazinecarbothioamide (1.5 g, 88%) as pale yellow solid. MS (ESI, pos. ion) m/z: 322.1 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 12.90 (brs, 1H), 10.43 (brs, 1H), 9.19 (s, 1H), 8.75 (s, 1H), 8.71 (s, 1H), 7.87-7.93 (m, 1H), 7.76 (d, 1H, J=8.4 Hz), 7.62 (d, 1H, J=8.4 Hz), 4.40-4.53 (m, 1H), 1.11 (d, 6H, J=6.6 Hz).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 h
  3. customThe mixture was quenched with water (20 mL)
  4. customto get a pale yellow precipitate
  5. filtrationThe precipitate was filtered
  6. washwashed with water (2×10 mL)
  7. customdried
  8. additionThe crude product was treated with 20% EtOAc in petroleum ether (2×20 mL)

Sources & evidence

ORD record
ord-48104e19cc8d475abca2ef3ea9d75192
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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