Ethyl Acetate → HCID 59463465, compound

HRID 1713050Notes

Reaction equation

HRID 1713050 reaction equation
[C:1](Cl)(Cl)=[S:2].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:21][C:20]3[CH:19]=[C:18]([C:22]([NH:24][NH2:25])=[O:23])[NH:17][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1)([O-:7])=[O:6].C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>C1COCC1.O>[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:21][C:20]3[CH:19]=[C:18]4[N:17]([C:1](=[S:2])[NH:25][NH:24][C:22]4=[O:23])[C:16]=3[CH:15]=2)=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 59463464HCID 59463464, compound

Product 1

HCID 59463465HCID 59463465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

As depicted in Scheme 29 below, a solution of thiophosgen (1.2 molequivalents) in THF is added dropwise at room temperature to a stirred solution of the corresponding hydrazide, 2-(4-nitrophenyl)-4H-furo[3,2-b]pyrrole-5-carbohydrazide, prepared as described hereinabove (1.5 molequivalents), and Na2CO3 in dry THF. The mixture is stirred for 12 hours, and thereafter a mixture of ethyl acetate and water is added. The organic phase is washed with diluted HCl and brine and concentrated wider reduced pressure. The pure product, 2-(4-nitro-phenyl)-4-thioxo-5,6-dihydro-4H-1-oxa-3b,5,6-triaza-cyclopenta[a]inden-7-one, is obtained after purification by flash chromatography.

Workup

  1. customprepared
  2. additionis added
  3. washThe organic phase is washed with diluted HCl and brine
  4. concentrationconcentrated wider reduced pressure

Sources & evidence

ORD record
ord-018120ce7d064b24ae1ce2c34609464a
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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