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Hydrochloric Acid → 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetic acid

HRID 1274598
Notes
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Reaction equation

HRID 1274598 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][C:22]([O:24]CC)=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28].Cl>ClCCCl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][C:22]([OH:24])=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11729347Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

Product 1

HCID 221199035-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate (0.600 g), 10% hydrochloric acid (20.0 mL), and 1,2-dichloroethane (2.00 mL) is boiled for 30 minutes while allowing the 1,2-dichloroethane to evaporate, cooled, and poured onto ice. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and air-dried to give the title product as a white solid (0.550 g, mp 240-242° C.).

Workup

  1. customto evaporate
  2. temperaturecooled
  3. additionpoured onto ice
  4. filtrationThe resultant aqueous mixture is filtered
  5. customto obtain a solid
  6. washThe solid is washed with water
  7. customair-dried

Sources & evidence

ORD record
ord-91a662af98054948bd33ff86650e14fb
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06156700

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes