Hydrochloric Acid → HCID 11391634, compound

HRID 551717Notes

Reaction equation

HRID 551717 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[CH2:14]([SH:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C(=O)C>[CH2:14]([S:22][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81441-OctanethiolHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 11391634HCID 11391634, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

While cooling a reaction vessel on a water bath, were mixed 17.3 g (100 mmol) of 4-nitrophthalonitrile, 15.7 g (110 mmol) of 1-octanethiol, 20.7 g (150 mmol) of potassium carbonate and 80 ml of N,N-dimethylacetamide. The resultant mixture was stirred for 7 hours at room temperature and then for 1 hour at 40° C. The thus-obtained reaction mixture was poured into 600 ml of a 3% hydrochloric acid. The resultant precipitates were separated by a filtration under reduced pressure, and then washed with water and dried. Thereafter, by recrystallization from a mixed solvent of methanol (190 ml)/water (9 ml), there was obtained 18.5 g (Yield: 68%) of white powder synthesis intermediate (A-1) (Melting point=37 to 38° C.).

Workup

  1. temperatureWhile cooling a reaction vessel on a water bath
  2. customThe thus-obtained reaction mixture
  3. customThe resultant precipitates
  4. customwere separated by a filtration under reduced pressure
  5. washwashed with water
  6. customdried
  7. customThereafter, by recrystallization from a mixed solvent of methanol (190 ml)/water (9 ml)
  8. customthere was obtained

Sources & evidence

ORD record
ord-6bbefa36595a4352bf94931a18fe2a0f
Source dataset
uspto-grants-2011_05
Patent number
US07947826B2

Reaction notes

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