1-Butanol → HCID 178430462, compound

HRID 1926618Notes

Reaction equation

HRID 1926618 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:22]#[N:23])=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:12][C:13]=1[CH:14]=O.C(O)CCC.[NH2:29][CH2:30][CH:31]([NH2:33])[CH3:32].II.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:22]#[N:23])=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:12][C:13]=1[C:14]1[NH:29][CH2:30][CH:31]([CH3:32])[N:33]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 807IodineHCID 6567PropylenediamineHCID 11430Potassium CarbonateHCID 86640156HCID 86640156, compound

Product 1

HCID 178430462HCID 178430462, compoundYield 32%

Procedure

To 4-(2,4-dichlorophenyl)-5-formyl-2-morpholin-4-ylthiophene-3-carbonitrile (52.0 mg, 0.000142 mol) in tent-butyl alcohol (0.75 g, 0.010 mol) was added 1,2-diaminopropane (12.9 mg, 0.000174 mol) and the mixture was stirred for 30 min. Iodine (51 mg, 0.00020 mol) and potassium carbonate (65.7 mg, 0.000475 mol) was added the mixture was stirred at 70° C. for 3 hr. The reaction mixture was quenched by saturated sodium bicarbonate solution and brine. The organic layer was collected and purified by column chromatography to afford 4-(2,4-dichlorophenyl)-5-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)-2-morpholinothiophene-3-carbonitrile (19 mg, 32%). LCMS: (FA) ES+ 421. 1H NMR (400 MHz, d1-chloroform) δ: 7.60 (s, 1H), 7.50-7.40 (m, 1H), 7.40-7.30 (m, 1H), 4.20-4.05 (m, 1H), 3.90-3.75 (m, 5H), 3.60-3.70 (m, 4H), 3.38-3.20 (m, 1H), 1.25 (s, 3H).

Workup

  1. stirringwas stirred at 70° C. for 3 hr
  2. customThe reaction mixture was quenched by saturated sodium bicarbonate solution and brine
  3. customThe organic layer was collected
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-dc65b01468b9488c9beb7890a8d2c441
Source dataset
uspto-grants-2012_05
Patent number
US08183240B2

Reaction notes

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