Cyanamide → HCID 88949240, compound

HRID 1844672Notes

Reaction equation

HRID 1844672 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[O:5][C:6]1[CH:7]([CH2:20][CH:21]2[CH2:26][CH2:25][S:24][CH2:23][CH2:22]2)[NH:8][C:9](=[O:19])[C:10]=1[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:2].[NH2:28][C:29]#[N:30].C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:1]([O:3][C:4](=[O:27])[O:5][C:6]1[CH:7]([CH2:20][CH:21]2[CH2:26][CH2:25][S:24](=[N:30][C:29]#[N:28])[CH2:23][CH2:22]2)[NH:8][C:9](=[O:19])[C:10]=1[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:2]

Participants

6

Reactant 3

HCID 9864CyanamideHCID 76724Iodobenzene diacetateHCID 68299279HCID 68299279, compound

Product 1

HCID 88949240HCID 88949240, compound

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of carbonic acid 4-(2,5-dimethyl-phenyl)-5-oxo-2-(tetrahydro-thiopyran-4-ylmethyl)-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (compound P1.2) (184 mg, 0.47 mmol), NH2CN (40 mg, 0.95 mmol), (diacetoxyiodo)benzene (247 mg, 0.76 mmol), MgO (75 mg, 1.87 mmol) and rhodium acetate (10 mg, 0.02 mmol) in 10 ml of CH2Cl2 was stirred at room temperature for 2 h. Then, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by chromatography on silica gel. Yield: 110 mg of carbonic acid 2-(1-cyanoimino-hexahydro-1λ4-thiopyran-4-ylmethyl)-4-(2,5-dimethyl-phenyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl ester ethyl ester (title compound P1.9) as a solid, mp 103-105° C.

Workup

  1. filtrationThen, the mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ed40fc63843645c1a4376990a4d9e28b
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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