2,4-Difluorophenyl isocyanate → HCID 19021746, compound

HRID 1109057Notes

Reaction equation

HRID 1109057 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 50.1%

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 5 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) δ 8.1-7.9(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=8 Hz).

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-e6a12d07934242b2ba9f609ae6a0bf5a
Source dataset
uspto-grants-1994_06
Patent number
US05318984

Reaction notes

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