Nitric Acid → HCID 10362873, compound

HRID 1684112Notes

Reaction equation

HRID 1684112 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][CH2:6][C:7]([NH:9][C:10]1[C:15]([O:16][CH3:17])=[C:14]([C:18](=[O:21])[NH:19][CH3:20])[CH:13]=[C:12]([O:22][CH3:23])[C:11]=1[C:24](=[O:27])[NH:25][CH3:26])=[O:8]>>[Cl:5][CH2:6][C:7]([NH:9][C:10]1[C:15]([O:16][CH3:17])=[C:14]([C:18](=[O:21])[NH:19][CH3:20])[C:13]([N+:1]([O-:4])=[O:2])=[C:12]([O:22][CH3:23])[C:11]=1[C:24](=[O:27])[NH:25][CH3:26])=[O:8]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 10066058HCID 10066058, compound

Product 1

HCID 10362873HCID 10362873, compound

Conditions

Temperature
0 °C

Procedure

To 50 mL of red fuming nitric acid, chilled to 0° C., was added 2.3 g (6.69 mmol) of 30. After stirring at 0° C. for 45 minutes, 100 mL of ice water was added and the mixture quickly extracted with ethyl acetate. The ethyl acetate extract was dried over Na2SO4, evaporated down to a small volume, and placed on a silica gel column. Gradient chromatography (ethyl acetate to 5% methanolic ethyl acetate) afforded the desired product as a pure white solid: 1.5 g (58%) yield; TLC (ethyl acetate-methanol [9:1]), Rf =0,40; mp 259°-260° C.; IR (KBr pellet) 3370, 1676, 1651, 1568, 1534, 1472, 1404, 1373, 1315, 1054 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ9.99 (1H, s, acetamido proton), 8.64 and 8.28[2H, 2 s, J=2.3 Hz, 1- and 4-carbamyl protons, no assignments made), 4.25 (2H, s, methylene), 3.79 and 3.68 (6H, 2 s, 3- and 6-methoxys, no assignments made), 2.73 (6H, 2 overlapping d, J=4.4 Hz, 1- and 4-carbamyl methyls, no assignments made); mass spectrum (EI mode), m/z 388 (P+, 390 (P+, 37Cl).

Workup

  1. extractionthe mixture quickly extracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated down to a small volume

Sources & evidence

ORD record
ord-2ded28312f5146e78a3beceecece5a46
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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