Diiodomethane → 1-(3,5-Bis-trifluoromethyl-benzyl)-5-iodo-1H-imidazole-4-carbonitrile

HRID 349268

Reaction equation

HRID 349268 reaction equation
N[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:5]=[N:4][C:3]=1[C:22]#[N:23].C(I)[I:25].N(OCCC(C)C)=O>>[F:19][C:18]([F:21])([F:20])[C:10]1[CH:9]=[C:8]([CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=1)[CH2:7][N:6]1[C:2]([I:25])=[C:3]([C:22]#[N:23])[N:4]=[CH:5]1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 866012205-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carbonitrile

Product 1

HCID 866012221-(3,5-Bis-trifluoromethyl-benzyl)-5-iodo-1H-imidazole-4-carbonitrile

Procedure

Combine 5-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carbonitrile (0.066 g, 0.20 mmol), CH2I2 (3 mL), and isoamyl nitrite (250 μL, 2 mmol) in a round bottom flask and stir the mixture at 100° C. After 30 min., remove from heat and concentrate. Purify by flash chromatography on silica gel to give the title compound. MS (ES) 443.9 (M−1); 1H NMR (300 MHz, CDCl3) δ 7.93 (s, 1H), 7.78 (s, 1H), 7.58 (s, 2H), 5.31 (s, 2H).

Workup

  1. customremove
  2. temperaturefrom heat
  3. concentrationconcentrate
  4. customPurify by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e4fffbb3e46e4ebe834f378e2fba0e82
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Linked notes

Loading…