Dichloromethane → HCID 66748038, compound

HRID 2402143Notes

Reaction equation

HRID 2402143 reaction equation
[C:1]([C:3]1[C:4]([CH3:18])=[C:5]([C:14]([O:16][CH3:17])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].C(Cl)Cl.[Br:22]Br>>[Br:22][CH2:18][C:4]1[C:3]([C:1]#[N:2])=[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[S:6][C:5]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24408BromineHCID 66747691HCID 66747691, compound

Product 1

HCID 66748038HCID 66748038, compoundYield 96.6%

Procedure

To the solution of methyl 4-cyano-3-methyl-5-(morpholin-4-yl)thiophene-2-carboxylate (0.500 g, 1.88 mmol) in anhydrous methylene chloride (15 mL, 230 mmol) was added a solution of bromine (0.409 g, 2.56 mmol) in anhydrous methylene chloride (5.0 mL, 78 mmol). The mixture was stirred at room temperature for 4 days. The mixture was evaporated under reduced pressure and dried in vacuum to give a crude product that was used without further purification (0.658 g, contained 3.4% starting material, yield 96.6%). LC/MS: (FA) ES+ 345, 347. 1H NMR (400 MHz, d-chloroform) δ 4.83 (s, 2H), 3.87 (s, 3H), 3.85 (m, 4H), 3.62 (m, 4H).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customdried in vacuum

Sources & evidence

ORD record
ord-621f20e333d04c8db0cd34da50421111
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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