Ethanethiol → HCID 13910039, compound

HRID 231114Notes

Reaction equation

HRID 231114 reaction equation
[Na].[CH2:2]([SH:4])[CH3:3].O1CCCC1.[Cl:10][C:11]1[C:12]([NH:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29]Cl)=[CH:24][C:23]=2[CH3:31])=[N:13][CH:14]=[N:15][C:16]=1[CH3:17]>O>[Cl:10][C:11]1[C:12]([NH:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][S:4][CH2:2][CH3:3])=[CH:24][C:23]=2[CH3:31])=[N:13][CH:14]=[N:15][C:16]=1[CH3:17]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 20034502HCID 20034502, compound

Product 1

HCID 13910039HCID 13910039, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g of the sodium salt of ethyl mercaptan was added to 30 ml of anhydrous tetrahydrofuran. 1.7 g of 5-chloro-4-{2-[4-(2-chloroethyl)-2-methylphenoxy]ethylamino]-6-methylpyrimidine was added to the mixture, which was then heated for 3 hours whilst stirring. At the end of this time, water was added to the mixture, and the oily product which separated was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was removed by distillation under reduced pressure. The oily product obtained was subjected to column chromatography (Wakogen C-200, eluted with a 2:1 by volume mixture of toluene and ethyl acetate), to afford 1.2 g of the title compound as a pale yellow oily liquid, n20.8 =1.5478.

Workup

  1. temperaturewas then heated for 3 hours
  2. customthe oily product which separated
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed by distillation under reduced pressure
  7. customThe oily product obtained
  8. washeluted with a 2:1 by volume mixture of toluene and ethyl acetate),

Sources & evidence

ORD record
ord-138222848f5547ba87f711673f5ca1f5
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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