Cesium carbonate → 2-(2,6-Dichloro-3-(2-pyrrolidinoethoxy)phenylcarbonyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide hydrochloride

HRID 743469Notes

Reaction equation

HRID 743469 reaction equation
[Cs+].[Cl:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=[C:8]([Cl:20])[C:4]=1[C:5]([O-:7])=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:28][N:29]1[C:33](=[O:34])[CH:32]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[N:31]([CH3:40])[S:30]1(=[O:42])=[O:41]>CO>[ClH:2].[Cl:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:10][CH:9]=[C:8]([Cl:20])[C:4]=1[C:5]([O:7][CH2:28][N:29]1[C:33](=[O:34])[CH:32]([CH2:35][CH2:36][CH:37]([CH3:38])[CH3:39])[N:31]([CH3:40])[S:30]1(=[O:41])=[O:42])=[O:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 15817425HCID 15817425, compoundHCID 88140560HCID 88140560, compound

Product 1

HCID 194244322-(2,6-Dichloro-3-(2-pyrrolidinoethoxy)phenylcarbonyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,6-dichloro-3-(2-pyrrolidinoethoxy)-benzoic acid cesium salt (prepared by reaction of the acid (1.045 g, 3.069 mmol) in 30 ml of methanol with Cs2CO3 (1.2 g) followed by removal of the solvent) in DMF was added 2-chloromethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.75 g; 1.86 mmol) at room temperature. The resulting solution was allowed to react at room temperature under nitrogen for 17 hours. The mixture was concentrated in vacuo and the residue was dissolved in 70% ethyl acetate in ether, filtered, and washed with sodium bicarbonate solution and dried over sodium sulfate. The organic solution was concentrated, the residual clear oil dissolved in 40 ml of ether and treated with ether/HCl. The salt was purified from methanol/ether to afford 2-(2,6-dichloro-3-(2-pyrrolidinoethoxy)phenylcarbonyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide hydrochloride (Formula I: Ar=2,6-Cl2 -3-(OCH2CH2 -1-pyrrolidinyl)phenyl; R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3 ; as HCl salt) a solid, m.p. 161°-162° C.

Workup

  1. customfollowed by removal of the solvent) in DMF
  2. customto react at room temperature under nitrogen for 17 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 70% ethyl acetate in ether
  5. filtrationfiltered
  6. washwashed with sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. concentrationThe organic solution was concentrated
  9. dissolutionthe residual clear oil dissolved in 40 ml of ether
  10. additiontreated with ether/HCl
  11. customThe salt was purified from methanol/ether

Sources & evidence

ORD record
ord-622120d2b1194b51b07498678ab9fd84
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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