Ammonia → 2-({3-Nitro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}carbonyl)benzamide

HRID 2414308Notes

Reaction equation

HRID 2414308 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:27]([C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31]([OH:33])=O)=[O:28])[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][O:18][C:17]2=[O:26])[CH2:12][CH2:11]1)([O-:3])=[O:2].C(N1C=CN=C1)([N:40]1C=CN=C1)=O.N>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([C:27]([C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31]([NH2:40])=[O:33])=[O:28])[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:11][CH2:12][CH:13]([N:16]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][O:18][C:17]2=[O:26])[CH2:14][CH2:15]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 99357602-({3-Nitro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}carbonyl)benzoic acid

Product 1

HCID 101177972-({3-Nitro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}carbonyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from example 1 (0.9 g) and carbonyldiimidazole (1.1 equiv.) in dichloromethane (4 ml) was stirred at room temperature for 1 h, poured onto aqueous ammonia and stirred for a further 1 h. The mixture was extracted with ethyl acetate, the organics washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 2.5% methanol/dichloromethane. Yield 0.01 g as a solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organics washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 2.5% methanol/dichloromethane

Sources & evidence

ORD record
ord-b1b0cb5338974d56963290d1f4f5ddda
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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