Pyridine → Ethyl 2-(hydrazinecarboxamido)-4-methylthiazole-5-carboxylate

HRID 560546Notes

Reaction equation

HRID 560546 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[N:13]1[CH:18]=CC=CC=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[OH2:32].[NH2:33]N>O1CCCC1.ClCCl>[NH:13]([C:18]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)=[O:32])[NH2:33]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24654Hydrazine hydrate (1:1)HCID 821294-Nitrophenyl chloroformateHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 86635202Ethyl 2-(hydrazinecarboxamido)-4-methylthiazole-5-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (0.50 g, 2.68 mmol) and pyridine (0.32 mL, 4.03 mmol) in tetrahydrofuran (25 mL) and dichloromethane (25 mL) was added 4-nitrophenyl chloroformate (0.65 g, 3.22 mmol) at 0° C. The resulting reaction mixture was stirred at ambient temperature for 1 hour, followed by the addition of hydrazine monohydrate (3.00 mL, 59.9 mmol). The reaction mixture was stirred at ambient temperature for 18 hours and quenched with water (100 mL). The solid precipitated was filtered, washed with water and ethyl acetate and dried to afford the title compound in 78% yield (0.51 g): MS (ES+) m/z 245.2 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  3. customquenched with water (100 mL)
  4. customThe solid precipitated
  5. filtrationwas filtered
  6. washwashed with water and ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-5873d727bcd94a188d551601bbb85d30
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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