Water → HCID 59463447, compound

HRID 1713057Notes

Reaction equation

HRID 1713057 reaction equation
[S:1]=[C:2]1[N:13]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]2[C:4](=[CH:5][C:6]3[O:7][CH:8]=[CH:9][C:10]=3[N:11]=2)[S:3]1.[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O-:22])=[O:21].CCCCCC.O>C(#N)C.C(OCC)(=O)C>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([C:8]2[O:7][C:6]3[CH:5]=[C:4]4[C:12]([N:13]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:2](=[S:1])[S:3]4)=[N:11][C:10]=3[CH:9]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 7416NitrobenzeneHCID 8058HexaneHCID 59463471HCID 59463471, compound

Product 1

HCID 59463447HCID 59463447, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-10 °C

Procedure

4-(2-Thioxo-7-oxa-1-thia-3,4-diaza-s-indacen-3-yl)-butyric acid (0.2 mmol) was dissolved in dry acetonitrile (2 ml) under nitrogen atmosphere, and the solution was cooled to −10° C. Nitrosyltetrafluoroborate (NOBF4, 0.24 mmol) mixed in dry acetonitrile (1 ml) was added thereto, and the mixture turned red immediately. The resulting mixture was stirred for one hour at −10° C., and a mixture of nitrobenzene (0.4 mmol) and a solution of CuCl2 dihydrate (15 mmol) in acetonitrile (1 ml) was added dropwise. The reaction mixture was allowed to warm-up to 0° C., and TLC analysis using a 1:1 hexane:ethyl acetate mixture as eluent indicated complete conversion after 0.5-1.0 hours. Thereafter ethyl acetate and water were added, the organic and aqueous layers were separated, the organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure to give the crude product 4-[6-(4-nitro-phenyl)-2-thioxo-7-oxa-1-thia-3,4-diaza-s-indacen-3-yl]-butyric acid which was further purified by column chromatography using fine silica and a 4:1 hexane:ethyl acetate mixture as eluent.

Workup

  1. additionwas added
  2. temperatureto warm-up to 0° C.
  3. customafter 0.5-1.0 hours
  4. customthe organic and aqueous layers were separated
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e1c62f1c6e444bd4a5d590a364427c94
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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