Triethylamine → HCID 178443906, compound

HRID 622278Notes

Reaction equation

HRID 622278 reaction equation
C(N(CC)CC)C.[CH2:8]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].[C:27](Cl)(Cl)=[S:28]>C(Cl)(Cl)Cl>[CH2:8]([C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]2[CH:21]=[CH:22][C:23]([N:24]=[C:27]=[S:28])=[CH:25][CH:26]=2)[CH2:18][CH2:19]1)[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 178443904HCID 178443904, compound

Product 1

HCID 178443906HCID 178443906, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of 2.36 ml of triethylamine in 15 ml of chloroform was treated dropwise at -10° C. with a solution of 2.18 g of p-[trans-4-(5-hexenyl)cyclohexyl]aniline in 20 ml of chloroform. After 5 minutes the mixture was treated with a solution of 690 μl of thiophosgene in 10 ml of chloroform, warmed to room temperature and stirred for 2 hours. Thereafter, the reaction mixture was partitioned between water and chloroform. The organic phase was dried over magnesium sulphate and concentrated. Chromatographic separation on 140 g of silica gel using ethyl acetate/petroleum ether (vol. 5:95) and subsequent crystallization from 80 ml of methanol and low temperature filtration gave 1.24 g of p-[trans-4-(5-hexenyl)cyclohexyl]phenylisothiocyanate (purity 100%) as a milky liquid of m.p. (C-N) 15.2° C. and cl.p. (N-I) 46.1° C.

Workup

  1. customThereafter, the reaction mixture was partitioned between water and chloroform
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated
  4. customChromatographic separation on 140 g of silica gel
  5. customethyl acetate/petroleum ether (vol. 5:95) and subsequent crystallization
  6. filtrationfrom 80 ml of methanol and low temperature filtration

Sources & evidence

ORD record
ord-0fca5caa335041bfb8b3823900409754
Source dataset
uspto-grants-1988_09
Patent number
US04770503

Reaction notes

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