Methanol → HCID 53645391, compound

HRID 1378560Notes

Reaction equation

HRID 1378560 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH:10](Br)[C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1.[Cl:21][C:22]1C=C[C:25]([C:26](N)=S)=[CH:24][CH:23]=1.CO.[S:33]1[CH:37]=[CH:36]N=C1.C(#[N:40])C>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:40]=[C:37]([C:36]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:21])[S:33][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 6342AcetonitrileHCID 9256ThiazoleHCID 27348264-ChlorothiobenzamideHCID 53933001HCID 53933001, compound

Product 1

HCID 53645391HCID 53645391, compound

Procedure

A solution of the bromoketone intermediate from Step 3 (0.49 g, 1.3 mmol) and 4-chlorothiobenzamide (0.24 g, 1.4 mmol) in 5 mL of acetonitrile was heated to reflux for 3 hours. The solution was cooled to room temperature and poured into 20 mL of methanol, chilled with an ice bath, whereupon crystals of the thiazole formed which were isolated by filtration and air dried (0.31 g, 52%): mp 103°-105° C. 1H NMR (CDCl3) 300 MHz 8.31 (m, 1H), 7.50-7.60 (m, 2H), 7.36 (m, 2H), 7.23 (d, J=8.5 Hz, 2H), 7.19 (d, J=8.5 Hz, 2H), 6.94 (t, J=8.5 Hz, 1H), 6.83 (t, J=9.2 Hz, 1H) 2.48 (S,3H). 19F NMR (CDCl3) -108.50 (m), -109.49 (m). Mass spectrum M+H=430.

Workup

  1. temperatureto reflux for 3 hours
  2. customformed which
  3. customwere isolated by filtration and air
  4. customdried (0.31 g, 52%)

Sources & evidence

ORD record
ord-42dbe00dbca64acebb5eda569d6d17d8
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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