Triethylamine → HCID 178456604, compound

HRID 1447161Notes

Reaction equation

HRID 1447161 reaction equation
[CH:1]([NH:4][S:5](Cl)(=[O:7])=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:16]([NH:20][C:21](=[NH:30])[S:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(OC)=[O:17]>ClCCCl>[CH:1]([N:4]1[S:5](=[O:7])(=[O:6])[NH:30][C:21]([S:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:20][C:16]1=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117737Isopropylsulphamoyl chlorideHCID 140335038HCID 140335038, compound

Product 1

HCID 178456604HCID 178456604, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

37.9 parts of isopropylaminosulfonyl chloride and 26.3 parts of triethylamine were introduced simultaneously, through two feed lines, into a stirred mixture of 54 parts of N-carbomethoxy-S-benzyl-isothiourea and 740 parts of 1,2-dichloroethane, at from 5° to 10° C. After having been stirred for 4 hours at 25° C., the reaction mixture was extracted once with 200 parts of water and twice with 100 parts, each time, of 0.5 N hydrochloric acid. After drying, and concentrating under reduced pressure, 79 parts of N-carbomethoxy-N'-isopropylsulfamyl-S-benzyl-isothiourea of nD25 =1.5598, were obtained. This material crystallized on trituration with hexane, and the crystalline product melted at 76°-78° C. 76 parts of this product were dissolved in a mixture of 44 parts of 50% strength by weight sodium hydroxide solution and 200 parts of water and the reaction mixture was stirred for 5 minutes at 85° C. It was then cooled and acidified with 15% strength hydrochloric acid, and the oil which precipitated was taken up in methylene chloride. This solution was dried over magnesium sulfate, filtered through neutral alumina and concentrated under reduced pressure, giving 59.5 parts of 6-isopropyl-3-benzylmercapto-5,6-dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxide (86.3% of theory), of melting point 124°-130° C. This constitutes active ingredient No. 2.

Workup

  1. extractionthe reaction mixture was extracted once with 200 parts of water and twice with 100 parts
  2. customAfter drying
  3. concentrationconcentrating under reduced pressure, 79 parts of N-carbomethoxy-N'-isopropylsulfamyl-S-benzyl-isothiourea of nD25 =1.5598
  4. customwere obtained
  5. customThis material crystallized on trituration with hexane
  6. dissolution76 parts of this product were dissolved in a mixture of 44 parts of 50% strength by weight sodium hydroxide solution and 200 parts of water
  7. stirringthe reaction mixture was stirred for 5 minutes at 85° C
  8. temperatureIt was then cooled
  9. customthe oil which precipitated
  10. dry with materialThis solution was dried over magnesium sulfate
  11. filtrationfiltered through neutral alumina
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e1ad8f292f641119017e4a97dba4652
Source dataset
uspto-grants-1982_02
Patent number
US04316014

Reaction notes

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