Sodium Azide → 8-(2-Azidoacetyl)-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 909869Notes

Reaction equation

HRID 909869 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][C:13]1[C:22]2[NH:21][C:20](=[O:23])[CH2:19][O:18][C:17]=2[C:16]([C:24](=[O:27])[CH2:25]Cl)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C=O)C>[N:1]([CH2:25][C:24]([C:16]1[C:17]2[O:18][CH2:19][C:20](=[O:23])[NH:21][C:22]=2[C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:14][CH:15]=1)=[O:27])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 579891615-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 579889888-(2-Azidoacetyl)-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (1.18 g) was added to a suspension of 5-(benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (4.8 g) in DMF (50 mL) and stirred for 2 h. The mixture was poured onto ice/water and the resulting solid filtered off, washed with water and dried under vacuum at 40° C. to afford the subtitled compound as a light brown solid (4.6 g). 1H NMR (300 MHz, DMSO-d6) δ 10.42 (s, 1H), 7.55 (m, 2H), 7.48 (m, 1H), 7.43-7.29 (m, 3H), 6.97 (m, 1H), 5.31 (s, 2H), 4.69 (s, 2H), 4.63 (s, 2H).

Workup

  1. additionThe mixture was poured onto ice/water
  2. filtrationthe resulting solid filtered off
  3. washwashed with water
  4. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-4979079b592a4a98abb39a360aea4ccd
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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