2,4-Difluorophenyl isocyanate → HCID 19021746, compound

HRID 374054Notes

Reaction equation

HRID 374054 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][C:15]1[NH:16][C:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:19]=1)[CH2:2][CH2:3][CH3:4].[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[N:40]=[C:41]=[O:42]>CCCCCC>[CH2:1]([N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][C:15]1[NH:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:16]=1)[C:41]([NH:40][C:34]1[CH:35]=[CH:36][C:37]([F:39])=[CH:38][C:33]=1[F:32])=[O:42])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 19021759HCID 19021759, compound

Product 1

HCID 19021746HCID 19021746, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Part C. To a solution of N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamine (0.2 g, 0.00045 mol) in hexane (15 mL) was added, dropwise, a solution of 2,4-difluorophenylisocyanate (0.065 mL, 0.085 g, 0.00055 mol) in hexane (5 mL) and the reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under vacuum and the residue was chromatographed with 7:3 hexane-ethyl acetate and the resulting solid was recrystallized from acetonitrile and triturated with hexane to give the title compound (0.138 g, 0.00023 mol) as a white solid, mp 114°-115°. 1H NMR (CDCl3) δ8.1-7.9(m,1H), 7.6-7.2(m,11H), 6.95-6.75(m,2H), 6.5-6.4(m,1H), 3.4-3.1(m,6H), 1.8-1.3(m,16H), 1.0(t,3H,J=8Hz).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was chromatographed with 7:3 hexane-ethyl acetate
  3. customthe resulting solid was recrystallized from acetonitrile
  4. customtriturated with hexane

Sources & evidence

ORD record
ord-b6e0dbdfb9a04e9d8e13032ac19bd777
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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