Water → HCID 86706797, compound

HRID 876103Notes

Reaction equation

HRID 876103 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12]1([C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:17])[NH:15]1)(=[O:14])=[O:13].O>ClCCl.CC(C)=O>[NH2:9][C:10]([NH2:15])=[S:11].[C:1]([N:15]1[C:16](=[O:17])[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:12]1(=[O:13])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5143SaccharinHCID 68284Benzoyl isothiocyanate

Product 1

HCID 86706797HCID 86706797, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a 250 mL 3-neck RBF equipped with a condenser, magnetic stirrer, thermo-probe, nitrogen purge and pressure-equilibrated addition funnel was added benzoyl isothiocyanate (25.0 g, 0.150 mol) and saccharin (28.1 g, 0.150 mol) followed by dichloromethane (100 mL). The mixture was cooled in an ice-water bath at a temperature below 5° C., at which point water (28.1 g, 0.150 mol) and acetone as the solvent and dichloromethane (100 mL) were added slowly over a period of time of about 30 minutes. The ice-water bath was removed and the reaction mixture was stirred under a nitrogen purge overnight. The reaction mixture was then concentrated in vacuo at a temperature of 40° C. to provide a solid that was dried to constant weight in vacuo at a temperature of 50° C. and a pressure of <1 mTorr in a 37% yield.

Workup

  1. customTo a 250 mL 3-neck RBF equipped with a condenser, magnetic stirrer
  2. customthermo-probe, nitrogen purge
  3. additionwere added slowly over a period of time of about 30 minutes
  4. customThe ice-water bath was removed
  5. custompurge overnight
  6. concentrationThe reaction mixture was then concentrated in vacuo at a temperature of 40° C.
  7. customto provide a solid
  8. customthat was dried to constant weight in vacuo at a temperature of 50° C.

Sources & evidence

ORD record
ord-671f3b043aa448ce9aaa90744d56c037
Source dataset
uspto-grants-2015_03
Patent number
US08986847B2

Reaction notes

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