Ammonia → 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetamide

HRID 1274599Notes

Reaction equation

HRID 1274599 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)=[O:23])[C:17]=3[CH:25]=2)[C:3]1=[O:26].C(N1C=CN=C1)([N:29]1C=CN=C1)=O.[Cl-].[NH4+].N.Cl>O1CCCC1.CO.C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[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]([NH2:29])=[O:23])[C:17]=3[CH:25]=2)[C:3]1=[O:26]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 221199035-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetic acid

Product 1

HCID 221198695-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetic acid (0.960 g, 0.00250 mol) and 1,1'-carbonyldiimidazole (0.420 g, 0.00259 mol) in tetrahydrofuran is stirred at room temperature for 4.5 hours, treated with ammonium chloride (0.230 g, 0.00430 mol), stirred overnight at room temperature, treated with concentrated ammonia (1.00 mL), stirred for 5 minutes, acidified with 10% hydrochloric acid, and concentrated in vacuo to obtain a residue. The residue is diluted with a 5% methanol in methylene chloride solution and the resultant mixture is stirred for three hours and filtered to obtain a solid. The solid is washed with a 5% methanol in methylene chloride solution, slurried in water, filtered, and dried to give the title product as a white solid which is identified by NMR spectral analysis.

Workup

  1. stirringstirred overnight at room temperature
  2. stirringstirred for 5 minutes
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue
  5. filtrationfiltered
  6. customto obtain a solid
  7. washThe solid is washed with a 5% methanol in methylene chloride solution
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-69b9d7c892074a91beeb229378589c92
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

Loading…