Hydrazine hydrate (1:1) → Ethyl 5-(hydrazinecarboxamido)-3-methylthiophene-2-carboxylate

HRID 2067329Notes

Reaction equation

HRID 2067329 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8](OC2C=CC=CC=2)=[O:9])[S:4][C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].O.[NH2:23][NH2:24]>O1CCCC1>[NH:23]([C:8]([NH:7][C:5]1[S:4][C:3]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:2]([CH3:1])[CH:6]=1)=[O:9])[NH2:24]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 43403943Ethyl 3-methyl-5-(phenoxycarbonylamino)thiophene-2-carboxylate

Product 1

HCID 66631914Ethyl 5-(hydrazinecarboxamido)-3-methylthiophene-2-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of ethyl 3-methyl-5-(phenoxycarbonylamino)-thiophene-2-carboxylate (18.89 g, 61.86 mmol) in tetrahydrofuran (130 mL) was added hydrazine monohydrate (19.0 mL, 391.7 mmol). The resulting reaction mixture was stirred for 2.5 h, and then concentrated in vacuo. The residue was triturated with ethyl acetate to afford ethyl 5-(hydrazinecarboxamido)-3-methylthiophene-2-carboxylate as a yellowish solid in 89% yield (13.30 g): MS (ES+) m/z 244.2 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-d0f4d7d2d41040859ee0ead76e57f82e
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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