TFA dichloromethane water → 6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2-thioxo-1,3-diazaspiro[4.4]nonan-4-one

HRID 489234Notes

Reaction equation

HRID 489234 reaction equation
C(OC([N:8]1[C:12]2([CH2:16][CH2:15][CH2:14][CH:13]2[C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[C:11](=[O:24])[N:10]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)[C:9]1=[S:33])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.O>>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][C:12]32[NH:8][C:9](=[S:33])[N:10]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)[C:11]3=[O:24])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 18672661TFA dichloromethane waterHCID 235885626-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester

Product 1

HCID 220252886-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2-thioxo-1,3-diazaspiro[4.4]nonan-4-oneYield 60.4%

Procedure

6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-4-oxo-2-thioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (42 mg, 74 μmol) (Preparation 10) was added to a TFA/DCM/H2O (1/1/0.1) solution (1 ml) at RT. After 30 min the reaction mixture was concentrated to give a beige solid which was washed with pentane to yield 6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2-thioxo-1,3-diazaspiro[4.4]nonan-4-one (21 mg, beige solid). 1H NMR (CDCl3): 8.39 (1H, s), 7.51 (2H, d, J=8.4 Hz), 7.35 (1H, m), 7.19 (2H, d, J=8.4 Hz), 6.44 (2H, m), 3.36 (1 H, dd, J1=12.9 Hz, J2=6.1 Hz), 2.45-2.65 (2H, m), 1.8-2.25 (4H, m).

Workup

  1. concentrationAfter 30 min the reaction mixture was concentrated
  2. customto give a beige solid which
  3. washwas washed with pentane

Sources & evidence

ORD record
ord-391d1df744114136a458eae9aa7689be
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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