Ammonia → HCID 57825048, compound

HRID 1668706Notes

Reaction equation

HRID 1668706 reaction equation
II.[Br:3][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][CH2:18][CH2:17][C:16]=3[CH:20]=2)=[CH2:11])[CH:7]=[CH:8][CH:9]=1.[NH3:21].C([O:25][CH2:26]C)(=O)C.C(#[N:30])C>C(OCC)(=O)C.[Ag]OC#N>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([C:12]3[CH:13]=[CH:14][C:15]4[O:19][CH2:18][CH2:17][C:16]=4[CH:20]=3)[CH2:11][O:25][C:26]([NH2:30])=[N:21]2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 21930812Acetonitrile ethyl acetateHCID 578250555-[1-(3-Bromo-phenyl)-vinyl]-2,3-dihydro-benzofuran

Product 1

HCID 57825048HCID 57825048, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178513473HCID 178513473, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to general method 2, a solution of iodine in ethyl acetate was added to a mixture of 5-[1-(3-bromo-phenyl)-vinyl]-2,3-dihydro-benzofuran (3.5 g, 11.6 mmol) and silver cyanate in ethyl acetate/acetonitrile. The crude product of this reaction was subsequently reacted with aqueous ammonia (30% by Vol). Purification by SCX column yielded 1.5 g of product (37%).

Workup

  1. customPurification by SCX column

Sources & evidence

ORD record
ord-2fd7ea4589364a4e9b8547f64c6569ef
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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