Ammonia → HCID 15221493, compound

HRID 1110105Notes

Reaction equation

HRID 1110105 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]([C:17](=[O:25])[CH2:18][N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:6]=12.[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]Br.C(N(CC)CC)C.N>CO.C(Cl)(Cl)Cl>[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]([C:17](=[O:25])[CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][Br:26])[CH2:21][CH2:20]3)[C:6]=12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 2214831,10-DibromodecaneHCID 19019103HCID 19019103, compound

Product 1

HCID 15221493HCID 15221493, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of 38 (20 mg, 57 μmol), 1,10-dibromodecane (0.22 g. 0.73 mmol), and triethylamine (0.2 mL) was stirred in MeOH (0.5 mL) at 25° C. for 3 days. The reaction was judged complete by TLC (Rf of product on silica, with chloroform:methanol:ammonia, 90:10:1, by volume was 0.66), and all volatile materials were removed in vacuo. The remaining residue was dissolved in 0.5N HCl. The acidic aqueous layer was washed with ether (2×), and then made basic (=pH 9) by addition of 10% sodium carbonate. The product was extracted into CHCl3 (3×), and the combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to give the crude product as a glass. Yield 20 mg (61%).

Workup

  1. customall volatile materials were removed in vacuo
  2. dissolutionThe remaining residue was dissolved in 0.5N HCl
  3. washThe acidic aqueous layer was washed with ether (2×)
  4. additionby addition of 10% sodium carbonate
  5. extractionThe product was extracted into CHCl3 (3×)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-0801eefcbb9d4063bf650f9442722065
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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