Potassium Hydroxide → HCID 86761312, compound

HRID 547840Notes

Reaction equation

HRID 547840 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[OH-].[K+].[N:10](=[C:12]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:13]1[CH:32]=[CH:31][C:16]([CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])=[CH:15][CH:14]=1)[NH2:11]>C(O)C.C1COCC1.[Hg]=O>[N+:10](=[C:12]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:13]1[CH:14]=[CH:15][C:16]([CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])=[CH:31][CH:32]=1)=[N-:11]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 86761311HCID 86761311, compound

Product 1

HCID 86761312HCID 86761312, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a vigorously stirred mixture of yellow mercury oxide (0.18 g, 0.8 mmol), sodium sulfate (0.14 g, 1 mmol) and sat. KOH in ethanol (1 ml) was added a solution of (XII) (0.27 g, 0.7 mmol) in THF (10 ml). The mixture was stirred for 16 h. in the dark, then filtered through a pad of celite. The filtrate was collected and concentrated in vacuo to yield (XIII) (0.27 g, 100%) as a dark red solid; m.p. 111-115° C., decolurises at 136° C.; δ H (CDCl3, 200 MHz) 3.43 (m, 2H, CH2CH2NH), 3.69 (m, 2H, CH2CH2O), 4.49 (s, 2H, ArCH2O), 5.80 (bs, 1H, CH2NHC(O)), 7.02 (m, 1H, 4″-H), 7.41-7.44 (m, 13H, Ar—H), 7.44 (s, 1H, ArNHC(O)) ppm; δC (CDCl3, 400 MHz) 40.3 (CH2NH), 62.4 (CH2CH2O), 68.0 (ArCH2O), 120.3 (4″-C), 123.2 (4′-C), 125.0, 125.8, 126.5, 126.7 (2-, 2′-, 2″-, 6-, 6′-, 6″-C), 128.9, 129.1, 129.2, 129.3 (1-, 1′-, 3-, 3′-, 3″-, 5-, 5′-, 5″-C), 135.0, 138.9 (4-, 1″-C), 156.5 (NHC(O)NH) ppm; υmax 3344 (N—Hstr), 2042 (R2C═N═N), 1658 ((R(H)N)2C═Ostr) cm−1; m/z 445 [M+MeCN+NH4]+ (100%).

Workup

  1. filtrationfiltered through a pad of celite
  2. customThe filtrate was collected
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b1f0434113e4112b594cc109920ecd7
Source dataset
uspto-grants-2011_05
Patent number
US07939581B2

Reaction notes

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