1,3-Cyclohexadiene → HCID 44283041, compound

HRID 2105537Notes

Reaction equation

HRID 2105537 reaction equation
C([O:8][N:9]([CH2:12][CH:13]1[C:18](=[O:19])[NH:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[S:14]1)[CH:10]=[O:11])C1C=CC=CC=1.C1CCC=CC=1>CCO.[Pd]>[OH:8][N:9]([CH2:12][CH:13]1[C:18](=[O:19])[NH:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[S:14]1)[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 86600475HCID 86600475, compound

Product 1

HCID 44283041HCID 44283041, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-benzyloxy-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-ylmethyl)-formamide (0.17 mmol) in EtOH (12 mL) is added Pd/C (10%) (88.5 mg) followed by cyclohexadiene (1.8 mL). The reaction mixture is stirred at room temperature for 12 hours and the final product N-hydroxy-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-ylmethyl)-formamide is obtained by preparative LC/MS using 1 to 99% ACN as gradient. 1H NMR (400 MHz, MeOD): δ 8.48 (s, 0.4H), 7.97 (s, 0.6H), 7.49 (m, 2H), 7.19 (m, 2H), 4.03 (m, 2H), 3.5 (dd, 1H). MS: (ES+): 239.1[M+1].

Sources & evidence

ORD record
ord-4b0e438999924a4c9459949d6a7593c9
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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