HCID 90418191, compound → HCID 90418688, compound

HRID 2177304Notes

Reaction equation

HRID 2177304 reaction equation
Cl[C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[F:16])[S:4][N:3]=1.[O:17]([CH3:19])[Na]>CO>[F:16][C:10]1[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=1[C:5]1[S:4][N:3]=[C:2]([O:17][CH3:19])[C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 90418191HCID 90418191, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 90418688HCID 90418688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Into a 250-mL round-bottom flask, was placed 3-chloro-5-(2-fluoro-4-methylphenyl)-1,2-thiazole-4-carbonitrile (2.0 g, 7.91 mmol, 1.00 equiv), methanol (100 mL), NaOCH3 (2.1 g, 38.87 mmol, 4.91 equiv). The resulting solution was stirred for 3 h at 75° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 1.5 g (76%) of 5-(2-fluoro-4-methylphenyl)-3-methoxy-1,2-thiazole-4-carbonitrile as a white solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 1.5 g (76%) of 5-(2-fluoro-4-methylphenyl)-3-methoxy-1,2-thiazole-4-carbonitrile as a white solid

Sources & evidence

ORD record
ord-5377bac638654a78b72d211e4e29d387
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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