1,1'-Carbonyldiimidazole → HCID 86601203, compound

HRID 730386Notes

Reaction equation

HRID 730386 reaction equation
NC1C=CC(C2N(C)C(C#N)=CC=2)=CC=1C(O)(C)C.C1N=CN(C(N2C=NC=C2)=[S:26])C=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:44][C:45]1([CH3:63])[C:50]2[CH:51]=[C:52]([N:55]3[CH:59]=[CH:58][CH:57]=[C:56]3[C:60]#[N:61])[CH:53]=[CH:54][C:49]=2[NH:48][C:47](=O)[O:46]1>C1COCC1>[CH3:44][C:45]1([CH3:63])[C:50]2[CH:51]=[C:52]([N:55]3[CH:59]=[CH:58][CH:57]=[C:56]3[C:60]#[N:61])[CH:53]=[CH:54][C:49]=2[NH:48][C:47](=[S:26])[O:46]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 11499831HCID 11499831, compoundHCID 66593890HCID 66593890, compound

Product 1

HCID 86601203HCID 86601203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[4-amino-3-(1-hydroxy-1-methyl-ethyl)-phenyl]-1-methyl-1H-pyrrole-2-carbonitrile prepared according to Example 2 is dissolved in THF and TCDI or CDI is added. Extraction using an aqueous dilute hydrochloride solution gives an about quantitative yield of (4,4-dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-2-carbonitrile and (4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-2-carbonitrile, respectively.

Workup

  1. extractionExtraction

Sources & evidence

ORD record
ord-33afb4ce774b4feaad36fa8559e919e9
Source dataset
uspto-grants-2009_09
Patent number
US07582755B2

Reaction notes

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