Ammonium Hydroxide → HCID 58124866, compound

HRID 1971680Notes

Reaction equation

HRID 1971680 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16]([N:18]([CH2:22][CH2:23][N:24]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:25][C:26]#[C:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[CH:19]([CH3:21])[CH3:20])=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:41][CH3:42].C(N(CCC#CC1SC=CC=1)C(=O)C(N1CCC2C(=CC([N+]([O-])=O)=C(OC)C=2)C1C(OCC)=O)=O)(C)(C)C.C([O-])(=O)C.[Na+].[NH4+].[OH-]>C(OC(=O)C)(=O)C.O>[Br:1][C:2]1[C:3]([O:41][CH3:42])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:15]4[C:16](=[O:17])[N:18]([CH:19]([CH3:20])[CH3:21])[CH2:22][CH2:23][N:24]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:25][C:26]=4[C:27]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)=[C:9]3[C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 58124791HCID 58124791, compoundHCID 58124835HCID 58124835, compound

Product 1

HCID 58124866HCID 58124866, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 600 mg of 10k in 8 ml of acetic anhydride and 1g of anhydrous sodium acetate was heated under N2 for 45 min at 100° C. The reaction mixture was cooled and 20 ml of water was added and the mixture was stirred for another 1 hr at ambient temperature. The reaction mixture was then treated with cold conc. aq. NH4OH to make it slightly basic and the product was extracted with ethyl acetate. The crude material thus isolated was purified by chromatography over silica gel, using a gradient of heptane/acetone as eluent. The product isolated, was triturated with diisopropyl ether and provided 350 mg of white crystalline 10l. Mp: 233-234° C., Rf 0.55 (toluene/ethylactetate 1/1). NMR (CDCl3) δ 1.25-1.45 (bs, 15, tertC4H9+isoC3H7), 3.87 (s, 3, OCH3), 4.65 (bm, 1, isoC3H7), 6.72 (bs, 1, Ar—H), 6.93 (bm, 1, thiophene-H), 7.15 (bm, 2, thiophene-H+Ar—H), 7.43 (bm, 1, thiophene-H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe product was extracted with ethyl acetate
  3. customThe crude material thus isolated
  4. customwas purified by chromatography over silica gel
  5. customThe product isolated
  6. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-40547f73a7a54e5fad6287187125a8e0
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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