Methanol → HCID 57688122, compound

HRID 2425943Notes

Reaction equation

HRID 2425943 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:10]([C:12]2[S:16][C:15]([C:17]([O:19]C)=O)=[CH:14][CH:13]=2)=[O:11])=[CH:3][CH:2]=1.CO.O.[NH2:24][NH2:25]>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:10]([C:12]2[S:16][C:15]([C:17]([NH:24][NH2:25])=[O:19])=[CH:14][CH:13]=2)=[O:11])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)2×HCID 67087287HCID 67087287, compound

Product 1

HCID 57688122HCID 57688122, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-[2-(pyridin-4-yl)ethylcarbamoyl]thiophene-2-carboxylate (0.40 g, 1.4 mmol) was suspended in a liquid mixture of methanol (4.0 mL) and tetrahydrofuran (2.0 mL) and left at 55° C. until conversion to a homogeneous amber solution was confirmed. After addition of 80% hydrazine monohydrate (0.17 mL, 2.8 mmol), it was left at 55° C. for 24 hours. After addition of 80% hydrazine monohydrate (0.17 mL, 2.8 mmol), it was left at 55° C. for 4.5 hours and then at room temperature for 14 hours. The precipitated solid was recovered by filtration and dried to give the desired product, 5-hydrazinocarbonylthiophene-2-carboxylic acid (2-pyridin-4-yl)ethylamide (yield 82%).

Workup

  1. waitleft at 55° C. until conversion to a homogeneous amber solution
  2. waitwas left at 55° C. for 4.5 hours
  3. waitat room temperature for 14 hours
  4. filtrationThe precipitated solid was recovered by filtration
  5. customdried

Sources & evidence

ORD record
ord-f8166fae84204906b60d56a072a07c78
Source dataset
uspto-grants-2011_06
Patent number
US07968542B2

Reaction notes

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