Hydrochloric Acid → HCID 86711143, compound

HRID 624544Notes

Reaction equation

HRID 624544 reaction equation
[H-].[Na+].F[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[S:17][C:18]([CH3:23])=[CH:19][C:20]=1[C:21]#[N:22].Cl>C1COCC1>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([NH:15][C:16]2[S:17][C:18]([CH3:23])=[CH:19][C:20]=2[C:21]#[N:22])=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=1)#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 6890562-Amino-5-methyl-3-thiophenecarbonitrileHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 86711143HCID 86711143, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60%, 0.58 g) in THF (2 mL), was added 4-fluoro-3-nitro-benzonitrile (1.33 g, 8.0 mmol) and 2-amino-5-methyl-thiophene-3-carbonitrile (1.10 g, 8.0 mmol) in THF (10 mL), dropwise. The mixture was stirred at room temperature overnight. Two more batches of sodium hydride (60%, 0.50 g and 0.4 g) were added over the next 6 hours. After stirring for 3 days, the mixture was poured into ice-water (20 mL) and acidified to pH 3 with 6N hydrochloric acid (7 mL). The precipitate was filtered and washed with water. The solid was extracted with dichloromethane (35 mL). The solution was concentrated to a solid, and used in the next step without additional purification. LC-MS: m/z 285 (M+1), 307 (M+23). 1H NMR (CDCl3, 400 MHz): δ (ppm) 9.76 (s, 1H), 8.59 (s, 1H), 7.70 (d, 1H), 7.14 (d, 1H), 6.87 (s, 1H), 2.52 (s, 1H).

Workup

  1. stirringAfter stirring for 3 days
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. extractionThe solid was extracted with dichloromethane (35 mL)
  5. concentrationThe solution was concentrated to a solid
  6. customused in the next step without additional purification

Sources & evidence

ORD record
ord-e93c73c5d338414ca03089caa2ec9718
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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