Ethanethiol → HCID 13210512, compound

HRID 1462238Notes

Reaction equation

HRID 1462238 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:28]OC(=O)C(C)(C)C)[C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:17][CH:16]=2)[C:10](=[O:36])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1.[CH2:45]([SH:47])[CH3:46]>>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH2:28][S:47][CH2:45][CH3:46])[C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:19][CH:20]=2)[C:10](=[O:36])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 13210503HCID 13210503, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 13210512HCID 13210512, compoundYield 86.8%

Procedure

In 10 ml of ethyl mercaptan was dissolved 1.0 g of 1-benzyl-4-{4-[N-pivaloyloxymethyl-N-(2-pyrimidinyl)amino]benzyl}-2,3-dioxopiperazine, and 0.01 ml of 5.7 N hydrogen chloride-dioxane solution was added thereto, after which the resulting mixture was subjected to reaction at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was distilled under reduced pressure, and 50 ml of diisopropyl ether was added to the crystals thus obtained, after which the resulting crystals were filtered. The crystals thus obtained were recrystallized from isopropyl alcohol to obtain 0.8 g (86.8% yield) of white crystalline 1-benzyl-4-{4-[N-ethylthiomethyl-N-(2-pyrimidinyl)amino]benzyl}-2,3-dioxopiperazine having a melting point of 144° C.

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 3 hours
  3. customAfter the completion of the reaction
  4. distillationthe reaction mixture was distilled under reduced pressure, and 50 ml of diisopropyl ether
  5. additionwas added to the crystals
  6. customthus obtained
  7. filtrationafter which the resulting crystals were filtered
  8. customThe crystals thus obtained
  9. customwere recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-3c33942e5a684f19b44bd505e08dcda9
Source dataset
uspto-grants-1984_07
Patent number
US04459407

Reaction notes

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