Hydrazine → tert-Butyl 2-(2-hydrazinyl-2-oxoethyl)benzo[d]thiazole-6-carboxylate

HRID 1190850Notes

Reaction equation

HRID 1190850 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1)C.[NH2:23][NH2:24]>CO>[NH:23]([C:4](=[O:3])[CH2:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1)[NH2:24]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86707744tert-Butyl 2-(2-ethoxy-2-oxoethyl)benzo[d]thiazole-6-carboxylate

Product 1

HCID 86707745tert-Butyl 2-(2-hydrazinyl-2-oxoethyl)benzo[d]thiazole-6-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Compound 188b (480 mg, 1.5 mmol) in methanol (15 mL) was added anhydrous hydrazine (0.19 mL, 6.0 mmol) and the mixture stirred for 16 h. The resulting precipitate was filtered, washed with three volumes of methanol and dried in vacuo to afford Compound 188c (400 mg, 87%) as white powder. LCMS=1.64 min using analytical method (B), 308.0 (M+H). 1H NMR (400 MHz, CD3OD) δ 8.59 (d, J=1.1 Hz, 1H), 8.08 (dd, J=8.6, 1.8 Hz, 1H), 8.02-7.97 (m, 1H), 1.63 (s, 9H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with three volumes of methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c6a990134a3a4dcd93bc4c38ceb8f097
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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