Dimethylformamide → HCID 131723711, compound

HRID 2298640Notes

Reaction equation

HRID 2298640 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:14]=[C:15](C(N)=O)[S:16][C:17]=3[CH3:18])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:22]([O:26][C:27]([O:29]C(OC(C)(C)C)=O)=O)([CH3:25])([CH3:24])[CH3:23].C([N:40]([CH:43](C)C)CC)(C)C.C(=O)(O)[O-].[Na+].C[N:52](C)C=O>>[C:22]([O:26][C:27]([NH:52][CH:43]=[N:40][C:15]1[S:16][C:17]([CH3:18])=[C:13]([C:10]2[S:11][CH:12]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)[N:9]=2)[CH:14]=1)=[O:29])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 18537365HCID 18537365, compound

Product 1

HCID 131723711HCID 131723711, compoundYield 59%

Procedure

A stirred solution of 320 mg (1 mmol) of 4-[4-(3-hydroxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiophene-2-carboxamide was dissolved in dry dimethylformamide (50 mL) and treated with 262 mg (1.2 mmol) of di-tert-butyl-dicarbonate (Acros, Pittsburgh, Pa., USA) and diisopropylethylamine (261 μL, 1.5 mmol) for 64 hours at room temperature. The mixture was poured into sodium bicarbonate solution (200 mL) and extracted with dichloromethane (6×30 mL). The organic extracts were washed twice with brine (50 mL) and dried over anhydrous sodium sulfate. The solvents were in vacuo and column chromatography on silica gel (100 g) eluting with dichloromethane:methanol 95/5 (v:v) gave (tert-butoxy)-N-({4-[4-(3-hydroxyphenyl)(1,3-thiazol-2-yl)]-5-methyl(2-thienyl)}iminomethyl)carboxamide (247 mg, 59%) as a yellow oil. 1H-NMR (DMSO-d6; 300 MHz) δ9.56 (s, 1H), 9.12 (br s, 2H), 8.47 (s, 1H), 8.09 (s, 1H), 7.46 (m, 2H), 7.26 (m, 1H), 6.78 (m, 1H), 2.83 (s, 3H), 1.45 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C20H21N3O3S2 416.1 (M+H), found 415.7

Workup

  1. extractionextracted with dichloromethane (6×30 mL)
  2. washThe organic extracts were washed twice with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-32fb60c7f3344d68b2e8d4d634344308
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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