1-Propanol → 3-[4-Chloro-6-fluoro-2-propoxybenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1419707Notes

Reaction equation

HRID 1419707 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[H-].[Na+].Cl[C:8]1[S:9][C:10]2[C:16]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:18]3=[O:28])=[C:15]([F:29])[CH:14]=[C:13]([Cl:30])[C:11]=2[N:12]=1>O1CCCC1>[Cl:30][C:13]1[C:11]2[N:12]=[C:8]([O:4][CH2:1][CH2:2][CH3:3])[S:9][C:10]=2[C:16]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[NH:19][C:18]2=[O:28])=[C:15]([F:29])[CH:14]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24758Sodium hydrideHCID 109382113-[2,4-Dichloro-6-fluorobenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 153461793-[4-Chloro-6-fluoro-2-propoxybenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

108 ml of absolute n-propanol were added dropwise at room temperature to 1.1 g of sodium hydride (97% strength) in 40 ml of absolute tetrahydrofuran. Stirring was carried out for 30 minutes, after which 7.0 g of 3-[2,4-dichloro-6-fluorobenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (compound I.4) were slowly added. Stirring was carried out for 12 hours, after which the solvent was distilled off at reduced pressure and the residue was then taken up in water. 10% strength hydrochloric acid was added to the aqueous phase until the resulting pH was from 3 to 4. The precipitate formed was separated off, washed with water and then dried. Yield: 5.2 g.

Workup

  1. stirringStirring
  2. waitwas carried out for 12 hours
  3. distillationafter which the solvent was distilled off at reduced pressure
  4. addition10% strength hydrochloric acid was added to the aqueous phase until the resulting pH
  5. customThe precipitate formed
  6. customwas separated off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b22d4fb7bca04445a98ee8332890ff96
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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