Ammonia → (RS)-4-(3-Bromo-phenyl)-4-(4-difluoromethoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine

HRID 1668716Notes

Reaction equation

HRID 1668716 reaction equation
II.[Br:3][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([F:21])[F:20])=[C:14]([CH3:22])[CH:13]=2)=[CH2:11])[CH:7]=[CH:8][CH:9]=1.[NH3:23].C([O:27][CH2:28]C)(=O)C.C(#[N:32])C>C(OCC)(=O)C.[Ag]OC#N>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]([F:20])[F:21])=[C:14]([CH3:22])[CH:13]=3)[CH2:11][O:27][C:28]([NH2:32])=[N:23]2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 21930812Acetonitrile ethyl acetateHCID 578252414-[1-(3-Bromophenyl)vinyl]-1-difluoromethoxy-2-methylbenzene

Product 1

HCID 57825083(RS)-4-(3-Bromo-phenyl)-4-(4-difluoromethoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamineYield 85%

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 4-[1-(3-bromo-phenyl)-vinyl]-1-difluoromethoxy-2-methyl-benzene (4.9 g, 14 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 yielded 4.8 g of product (85%).

Workup

  1. customPurification by SCX

Sources & evidence

ORD record
ord-65205eec9f204b059d549925e402a213
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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