Water → HCID 15544616, compound

HRID 650266Notes

Reaction equation

HRID 650266 reaction equation
[S-:1][C:2]#[N:3].[Na+].BrBr.[Cl:7][C:8]1[NH:9][C:10]([CH3:15])=[CH:11][C:12]=1[C:13]#[N:14].O>CO>[Cl:7][C:8]1[NH:9][C:10]([CH3:15])=[C:11]([S:1][C:2]#[N:3])[C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516871Sodium thiocyanateHCID 15544615HCID 15544615, compound

Product 1

HCID 15544616HCID 15544616, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of sodium thiocyanate (7.5 g) in 50 ml of methanol was cooled to −76° C. Bromine in 30 ml of cold methanol was added dropwise over 12 min. A slurry of 2-chloro-3-cyano-5-methylpyrrole in 30 ml of cold methanol was added at once. After stirring 30 min at −78° C., the mixture was poured into H2O and stirred overnight, then filtered, washed with water and hexane, and air dried to afford 6.57 g of an off-white solid, m.p. 171° C.

Workup

  1. stirringstirred overnight
  2. filtrationfiltered
  3. washwashed with water and hexane, and air
  4. customdried

Sources & evidence

ORD record
ord-5667e2ec3a8747bb91906f9fd3c37ead
Source dataset
uspto-grants-2001_08
Patent number
US06271392B1

Reaction notes

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