Triethylamine → N-carbomethoxy-N'-isopropylsulfamyl-O-isopropyl-isourea

HRID 1447163

반응식

HRID 1447163 반응식
[CH:1]([NH:4][S:5](Cl)(=[O:7])=[O:6])([CH3:3])[CH3:2].[C:9]([NH:13][C:14](=[NH:19])[O:15][CH:16]([CH3:18])[CH3:17])([O:11][CH3:12])=[O:10].C(N(CC)CC)C>O1CCCC1>[C:9]([NH:13][C:14](=[N:19][S:5](=[O:7])(=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])[O:15][CH:16]([CH3:17])[CH3:18])([O:11][CH3:12])=[O:10]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 117737Isopropylsulphamoyl chlorideHCID 140335035methyl N-(C-propan-2-yloxycarbonimidoyl)carbamate

생성물 1

HCID 73682570N-carbomethoxy-N'-isopropylsulfamyl-O-isopropyl-isourea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

95 parts of isopropylaminosulfonyl chloride were stirred into a mixture of 96 parts of N-carbomethoxy-O-isopropylisourea and 73 parts of triethylamine in 700 parts of tetrahydrofuran in the course of 25 minutes, at 10°-15° C. After having been stirred for one hour at 25° C., the reaction mixture was extracted once with water and once with 0.5 N hydrochloric acid, dried and concentrated under reduced pressure. This gave 130 parts of N-carbomethoxy-N'-isopropylsulfamyl-O-isopropylisourea, of melting point 62°-64° C. 33.7 parts of this product were cyclized by means of 17.6 parts of 50% strength by weight sodium hydroxide solution in 30 parts of water in the course of 5 minutes at from 55° to 60° C. Extraction with ether, acidification, washing with water and drying gave 22 parts of 6-isopropyl-3-isopropoxy-5,6-dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxide, of melting point 164°-167° C. This constitutes active ingredient No. 4.

후처리

  1. extractionthe reaction mixture was extracted once with water and once with 0.5 N hydrochloric acid
  2. customdried
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e298007e4b2445ebbde4aacd382923e1
출처 데이터셋
uspto-grants-1982_02
특허 번호
US04316014

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