Hydrazine hydrate (1:1) → HCID 178509728, compound

HRID 38088Notes

Reaction equation

HRID 38088 reaction equation
[S:1]1CS[C:2]1=[C:5]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:6]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])=O.O.[NH2:23][NH2:24]>C(O)C>[SH:1][C:2]1[NH:24][N:23]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[C:5]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 229441233-(2-[1,3]Dithietan-2-ylidene-2-pyridin-4-yl-acetyl)-benzonitrile

Product 1

HCID 178509728HCID 178509728, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

3-(2-[1,3]Dithietan-2-ylidene-2-pyridin-4-yl-acetyl)-benzonitrile (5 g, 16.1 mmol) was suspended in absolute ethanol (50 mL) and heated to 60° C. Hydrazine monohydrate (3.13 mL, 64.4 mmol, 4 eq) was added dropwise and the mixture was stirred at 60° C. for 2 hours. The suspension was concentrated to about ¼ of the original volume, diluted with THF (50 mL) and stirred for 5 minutes. The yellow solid was filtered, washed with THF and dried at 50° C. for 1 hours. The crude product (4.59 g) was used in the following step without further purification.

Workup

  1. concentrationThe suspension was concentrated to about ¼ of the original volume
  2. additiondiluted with THF (50 mL)
  3. stirringstirred for 5 minutes
  4. filtrationThe yellow solid was filtered
  5. washwashed with THF
  6. customdried at 50° C. for 1 hours
  7. customThe crude product (4.59 g) was used in the following step without further purification

Sources & evidence

ORD record
ord-b5206da13d364368be9ce207f1374977
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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