Triethylamine → HCID 15041731, compound

HRID 1198832Notes

Reaction equation

HRID 1198832 reaction equation
[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[C:26](Cl)(Cl)=[S:27]>C(Cl)(Cl)Cl>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([N:16]=[C:26]=[S:27])=[CH:17][CH:18]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 15041730HCID 15041730, compound

Product 1

HCID 15041731HCID 15041731, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.256 g of p-(5-pentyl-2-pyridyl)aniline in 29 ml of chloroform was treated at 5° C. under nitrogen with 1.46 ml of triethylamine. Then, at 1° C. within 20 minutes a solution of 0.49 ml of 95 percent thiophosgene in 14.5 ml of chloroform was added dropwise to the reaction mixture so that the temperature did not exceed 3° C. The reaction mixture was subsequently stirred at room temperature for 45 minutes and under reflux for a further 40 minutes, then cooled and washed with 40 ml of 3N ammonia and with water. The aqueous phases were back-extracted with methylene chloride. The organic phases were dried over sodium sulphate, filtered and freed from solvent. Purification of the resulting brownish paste (1.56 g) by chromatography on 60 g of silica gel with 700ml of methylene chloride/hexane (vol. 1:1) and subsequent crystallization from diethyl ether/hexane gave 1.17 g of p-(5-pentyl-2-pyridyl)phenylisothiocyanate as colourless crystals with m.p. (C--SA) 36.3° C. and cl.p. (SA --I) 97.2° C.

Workup

  1. customdid not exceed 3° C
  2. temperatureunder reflux for a further 40 minutes
  3. temperaturecooled
  4. washwashed with 40 ml of 3N ammonia and with water
  5. extractionThe aqueous phases were back-extracted with methylene chloride
  6. dry with materialThe organic phases were dried over sodium sulphate
  7. filtrationfiltered
  8. customPurification of the resulting brownish paste (1.56 g) by chromatography on 60 g of silica gel
  9. customwith 700ml of methylene chloride/hexane (vol. 1:1) and subsequent crystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-c8489b945b4e4f8b9445e80a190803c3
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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