Methyl Ethyl Ketone → HCID 178477401, compound

HRID 266434

Reaction equation

HRID 266434 reaction equation
Br[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:4]1(=[O:6])=[O:5].[Na].[SH:16][C:17]1[N:21](C)[N:20]=[N:19][N:18]=1.[CH2:23](C(C)=O)C>>[CH3:23][CH:2]([S:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1)[N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:4]1(=[O:6])=[O:5]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 5360545SodiumHCID 15225519N-BromomethylsaccharinHCID 178482017HCID 178482017, compound

Product 1

HCID 178477401HCID 178477401, compoundYield 80%

Procedure

A mixture of 2-(bromomethyl) saccharin (3 g, 10.8 mmol) and the sodium salt of 5-mercapto-1-methyl-1H-tetrazole (1.49 g, 10.8 mmol) was heated under reflux in methyl ethyl ketone (75 ml) for 2 hours. The reaction mixture was cooled, poured into dilute sodium bicarbonate/ice solution and extracted with MDC (2x's). The combined organic extracts were dried (Na2SO4) and freed of solvent under vacuum. The crude product was chromatographed (silica gel-95:5 CH2Cl2 :ether), and the resultant oil was crystallized from hot isopropanol to afford 2.7 g (80%) of 2-(1-methyl-1H-tetrazol-5-ylthiomethyl)saccharin as a white solid, mp 106°-110° C. 1H nmr (90 MHz, CDCl3):5.55 (2H, s). FDMS: m/e 311 (M+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with MDC (2x's)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customThe crude product was chromatographed (silica gel-95:5 CH2Cl2 :ether)
  5. customthe resultant oil was crystallized from hot isopropanol

Sources & evidence

ORD record
ord-0bf9ae5e74be40eea0441baa6a95e8f8
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Linked notes

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