Water → HCID 22713342, compound

HRID 1278742Notes

Reaction equation

HRID 1278742 reaction equation
FC1C=CC([C:8]2[CH:13]=[C:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](C)=[C:19](C4C=CC(F)=CC=4)[CH:18]=3)(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=2[CH3:31])=CC=1.[O:32]1[C:36]2([CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[O:35][CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)N(C)CCC1>[C:9]1([CH3:31])[CH:10]=[CH:11][C:12]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([N:39]3[CH2:40][CH2:41][C:36]4([O:35][CH2:34][CH2:33][O:32]4)[CH2:37][CH2:38]3)=[CH:19][CH:18]=2)(=[O:15])=[O:16])=[CH:13][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decane2×HCID 69898801HCID 69898801, compound

Product 1

HCID 22713342HCID 22713342, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

To a solution of 4-fluorophenyl-4-tolylsulfone (1.25 g, 5 mmol) in N,N′-dimethylpropyleneurea (5 ml) was added 1,4-dioxa-8-aza-spiro[4.5]decane (0.88 g, 6 mmol), and potassium carbonate (0.83 g, 6 mmol). The mixture was stirred at room temperature for 4 h and then heated at 70° C. for 18 h. An additional 0.22 g of 1,4-dioxa-8-aza-spiro[4.5]decane was added, and the reaction was continued for 1 day. The mixture was cooled to room temperature, and treated with water. The resulting suspension was filtered, and the precipitate washed with water and methanol, and dried in vacuo to give 1.80 g of a white solid; m.p. 164-165° C.; MS (ES) m/z 373.9 (MH+); HRMS (EI) Calcd. for C20H23NO4S (M+): 373.1348, Found: 373.1342.

Workup

  1. temperatureheated at 70° C. for 18 h
  2. waitthe reaction was continued for 1 day
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe resulting suspension was filtered
  5. washthe precipitate washed with water and methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-28345cdb9250434898856ac308209248
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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