Borane;tetrahydrofuran → 6-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

HRID 1618642Notes

Reaction equation

HRID 1618642 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8][CH2:9][C:10](=O)[NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].B.C1COCC1>>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8][CH2:9][CH2:10][NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 41823566-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

Product 1

HCID 457916016-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Procedure

6-nitro-2H-benzo[b][1,4]thiazin-3(4H)-one (4 g, 19 mmol) was stirred in BH3-THF (285 mL, 258 mmol) at reflux overnight. After this time the reaction mixture was cooled to rt and quenched with MeOH. The reaction was partitioned between EtOAc and water. The separated organic layer was dried over Mg2SO4 and evaporated in vacuo to give 6-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine that was used without further purification in the next step. Mass Spectrum (ESI) m/e=197 (M+1).

Workup

  1. temperatureat reflux overnight
  2. customquenched with MeOH
  3. customThe reaction was partitioned between EtOAc and water
  4. dry with materialThe separated organic layer was dried over Mg2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-09883a05e25f434c859cd510e68e29cd
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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