Hydrochloric Acid → HCID 53768367, compound

HRID 1274651Notes

Reaction equation

HRID 1274651 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][O:22][CH2:23][C:24]([O:26]C)=[O:25])[C:17]=3[CH:28]=2)[C:3]1=[O:29].Cl>C(O)(=O)C>[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][O:22][CH2:23][C:24]([OH:26])=[O:25])[C:17]=3[CH:28]=2)[C:3]1=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54198540HCID 54198540, compound

Product 1

HCID 53768367HCID 53768367, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of {{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}methoxy}acetic acid, methyl ester (4.19 g, 0.00977 mol) and acetic acid is added 37% hydrochloric acid (5.00 ml). The resultant mixture is stirred overnight at 65° C. and cooled to room temperature. The mixture is concentrated in vacuo. The residue is suspended in water and quenched slowly by the addition of solid sodium bicarbonate to neutral pH. The resultant mixture is partitioned between ether and saturated sodium bicarbonate, and filtered. The filtrate is washed with methylene chloride, acidified with hydrochloric acid, and filtered to give the title product as a white solid (2.87 g, 70.7%, mp 191-192° C.) which is identified by NMR spectral analysis.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customquenched slowly by the addition of solid sodium bicarbonate to neutral pH
  3. customThe resultant mixture is partitioned between ether and saturated sodium bicarbonate
  4. filtrationfiltered
  5. washThe filtrate is washed with methylene chloride
  6. filtrationfiltered

Sources & evidence

ORD record
ord-64fa0ef40c4b4bd089acbde5fb63f7d9
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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