Acetic Acid → HCID 89761746, compound

HRID 528554Notes

Reaction equation

HRID 528554 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][C:13]2[CH:17]=[C:18]([S:21]([N:24]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])[CH:19]=[CH:20][C:12]1=2.C(O)(=O)C>C1COCC1.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][O:14][C:13]3[CH:17]=[C:18]([S:21]([N:24]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)[C:25]4[S:26][CH:27]=[CH:28][N:29]=4)(=[O:23])=[O:22])[CH:19]=[CH:20][C:12]2=3)=[C:2]([Br:1])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89761660HCID 89761660, compound

Product 1

HCID 89761746HCID 89761746, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

4-(2-bromo-4-nitrophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.025 g, 0.040 mmol) was dissolved in THF (0.135 mL) and acetic acid (0.127 mL, 2.227 mmol), and iron (0.023 g, 0.405 mmol) was added. The flask was sealed and heated to 70° C. for 1 hour. The reaction was cooled to rt, diluted with THF, and filtered through Celite® (diatomaceous earth), washing well with THF. The filtrate was concentrated, and partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The layers were separated, and the aqueous was then extracted (×2) with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to yield 4-(4-amino-2-bromophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a light brown solid. The material was carried forward without further purification. m/z (ESI) 587.1 (M+H)+.

Workup

  1. customThe flask was sealed
  2. temperatureThe reaction was cooled to rt
  3. filtrationfiltered through Celite® (diatomaceous earth)
  4. washwashing well with THF
  5. concentrationThe filtrate was concentrated
  6. custompartitioned between saturated aqueous sodium bicarbonate solution and EtOAc
  7. customThe layers were separated
  8. extractionthe aqueous was then extracted (×2) with EtOAc
  9. washThe combined organics were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-f16d7c2f7b4c4f5c9da992b361cc1939
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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