Dimethylformamide → HCID 10301777, compound

HRID 1069250Notes

Reaction equation

HRID 1069250 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH2:16]Br)=[C:14]([CH3:15])[C:10]=2[C:9]([C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([O:25][C:26](=[O:28])[CH3:27])=[C:20]([CH3:29])[CH:19]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:1][C:2]1[C:11]2[S:12][C:13]([CH2:16][N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])=[C:14]([CH3:15])[C:10]=2[C:9]([C:18]2[CH:19]=[C:20]([CH3:29])[C:21]([O:25][C:26](=[O:28])[CH3:27])=[C:22]([CH3:24])[CH:23]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 53735178HCID 53735178, compound

Product 1

HCID 10301777HCID 10301777, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic acid 4-(9-bromo-2-bromomethyl-3-methyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenyl ester (1.21 g, 2.27 mmol) was treated with diethylamine (0.71 mL, 6.82 mmol), potassium carbonate (0.94 g, 6.82 mmol), and N,N-dimethylformamide (12.1 mL). After 1 h at room temperature the reaction mixture was poured in water (250 mL), filtered, and rinsed well with water. Air drying gave the title compound as a yellow solid (1.13 g, 94.5%): NMR (DMSO-d6): δ8.19 (d, 1H), 7.66-7.61 (m, 1H), 7.47 (d, 2 H), 7.13 (s, 2H), 3.73 (s, 2H), 2.58-2.52 (q, 4H), 2.40 (s, 3H), 2.16 (s, 6H), 1.61 (s, 3H), 1.02 (t, 6H); MS(EI): [M+], 1 bromine isotope pattern, 523/525; Anal. Calc. for C28H30BrNO2S: C, 64.12; H, 5.77; N, 2.67. Found: C, 63.30, H, 5.67; N, 2.55.

Workup

  1. filtrationfiltered
  2. washrinsed well with water
  3. customAir drying

Sources & evidence

ORD record
ord-ce61aae555f647bca465abb8576de3ce
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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