Diethyl Ether → HCID 117759578, compound

HRID 1520110Notes

Reaction equation

HRID 1520110 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][N:7](C(OC(C)(C)C)=O)[C:8](=[O:19])[N:9]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.C(O[C:31](=[O:33])[CH3:32])(=O)C.[CH2:34](OCC)C>N1C=CC=CC=1>[C:8]([NH:9][C:10]1[CH:11]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[CH2:6][NH:7][C:31](=[O:33])[CH3:32])(=[O:19])[CH3:34]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 117759496HCID 117759496, compound

Product 1

HCID 117759578HCID 117759578, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound (14) (0.5 g, 2.5 mmol) in pyridine (5 mL) was added acetic anhydride (0.95 mL, 10 mmol), and the reaction was stirred overnight at room temperature. To the mixture was added diethyl ether (20 mL), and the mixture was washed successively with H2O (10 mL), 1M HCl (10 mL), and brine (10 mL). The organic layer was dried over Na2SO4 and evaporated to obtain 0.70 g (99%) of compound 15 as an off-white solid. IR (KBr) νmax. cm−1: 3312 (NH), 3042 (Ar—H), 1690 (C═O), 1522, 1410 (C═C). 1H NMR (500 MHz, CDCl3) S=2.11 (s, 3H, CH3); 2.23 (s, 3H, CH3); 5.05 (s, 2H, CH2); 7.46 (m, 2H, H-3, H-5); 7.89 (d, 1H, J=8.2 Hz, H-6). Calculated (%) for C11H13BrN2O2 (284.02); C: 46.33, H: 4.60, N: 9.82. found (%); C: 46.28, H: 4.63, N: 9.76.

Workup

  1. washthe mixture was washed successively with H2O (10 mL), 1M HCl (10 mL), and brine (10 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-2d5c80d1a4414c84952d1026ed52b367
Source dataset
uspto-grants-2015_07
Patent number
US09073900B2

Reaction notes

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