Water → HCID 178446938, compound

HRID 2083660Notes

Reaction equation

HRID 2083660 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][CH:9]=1.[CH2:14]([O:19][C:20]1[C:25]([C:26]2[C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:30][CH:29]=[C:28]([C:38]#[N:39])[CH:27]=2)=[CH:24][C:23]([C:40]#[N:41])=[CH:22][CH:21]=1)[CH2:15][CH2:16][CH2:17][CH3:18].O>CS(C)=O>[C:40]([C:23]1[CH:22]=[CH:21][C:20]([O:19][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:25]([C:26]2[C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:30][CH:29]=[C:28]([C:38](=[NH:39])[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=3)[CH:27]=2)[CH:24]=1)#[N:41]

Participants

6

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 24758Sodium hydrideHCID 20312725HCID 20312725, compound

Product 1

HCID 178446938HCID 178446938, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A slurry of sodium hydride (50% in oil, 1.76 g), m-aminobenzotrifluoride (5.91 g) and 6,6'-dipentyloxy[1,1'-biphenyl]-3,3'-dicarbonitrile (6.9 g; additional material is added to the batch of part (A) in 50 ml of anhydrous dimethylsulfoxide is stirred at room temperature for 3 days. The reaction mixture is poured into water and the resultant precipitate collected by filtration. The dried material is chromatographed on 1 liter of silica gel eluting with (1) dichloromethane and (2) 1% methanol/dichloromethane to yield 5'-cyano-2',6-bis(pentyloxy)-N-[3-(trifluoromethyl)phenyl][1,1'-biphenyl]-3-carboximidamide (melting point 74°-75° C after 2 recrystallizations from cyclohexane). The column is next eluted with 2% methanol/dichloromethane to yield 1.3 g of the desired product. Two recrystallizations of this material from 1% hydrochloric acid/methanol yields 900 mg of the title compound, melting point 207°-210° C.

Workup

  1. filtrationthe resultant precipitate collected by filtration
  2. customThe dried material is chromatographed on 1 liter of silica gel eluting with (1) dichloromethane and (2) 1% methanol/dichloromethane

Sources & evidence

ORD record
ord-f75a0fbf4d73460aa1b8ecddd73620f8
Source dataset
uspto-grants-1978_04
Patent number
US04086244

Reaction notes

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