Water → 2-[3-ethyl-6-fluoro-2(3H)-benzothiazolon-5-yl]tetrahydroimidazo[1,5-a]-pyridine-1,3(2H,5H)-dione

HRID 1761808Notes

Reaction equation

HRID 1761808 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([N:13]=[C:14]=[O:15])[C:10]([F:12])=[CH:11][C:6]=2[S:5][C:4]1=[O:16])[CH3:2].C([N:19]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:20]1[C:21](O)=[O:22])C.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([N:13]3[C:21](=[O:22])[CH:20]4[CH2:24][CH2:25][CH2:26][CH2:27][N:19]4[C:14]3=[O:15])[C:10]([F:12])=[CH:11][C:6]=2[S:5][C:4]1=[O:16])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 140142363-Ethyl-6-fluoro-2(3H)-benzothiazolon-5-yl isocyanateHCID 220165451-Ethylpiperidine-2-carboxylic acid

Product 1

HCID 140142372-[3-ethyl-6-fluoro-2(3H)-benzothiazolon-5-yl]tetrahydroimidazo[1,5-a]-pyridine-1,3(2H,5H)-dioneYield 52.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Ethyl-6-fluoro-2(3H)-benzothiazolon-5-yl isocyanate (1.16 g) and ethyl pipecolic acid (1.07 g) were dissolved in toluene (5 ml). A catalytic amount of triethylamine was added thereto, and the resultant mixture was stirred at 25° C. for 12 hours. Water was added to the reaction mixture, which was then extracted with toluene. The extract was dried and concentrated to give 2-[3-ethyl-6-fluoro-2(3H)-benzothiazolon-5yl]tetrahydroimidazo[1,5-a]-pyridine-1,3(2H,5H)-dione (0.89 g). m.p., 162°-164° C.

Workup

  1. extractionwas then extracted with toluene
  2. customThe extract was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c7b2d1aba0b5466c87b63e1dfb3e1284
Source dataset
uspto-grants-1989_05
Patent number
US04828605

Reaction notes

Loading…