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

HRID 1668724Notes

Reaction equation

HRID 1668724 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][CH3:19])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)=[CH2:11])[CH:7]=[CH:8][CH:9]=1.[NH3:24].C([O:28][CH2:29]C)(=O)C.C(#[N:33])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][CH3:19])=[C:14]([C:20]([F:21])([F:22])[F:23])[CH:13]=3)[CH2:11][O:28][C:29]([NH2:33])=[N:24]2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 21930812Acetonitrile ethyl acetateHCID 578251474-[1-(3-Bromo-phenyl)-vinyl]-1-methoxy-2-trifluoromethyl-benzene

Product 1

HCID 57825064(RS)-4-(3-Bromo-phenyl)-4-(4-methoxy-3-trifluoromethyl-phenyl)-4,5-dihydro-oxazol-2-ylamine

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-methoxy-2-trifluoromethyl-benzene (5.1 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 yield 4.6 g of product (67%).

Workup

  1. customPurification by SCX yield 4.6 g of product (67%)

Sources & evidence

ORD record
ord-a047c0957496401eb43a1709798585ce
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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