Hexane → 2-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione

HRID 27007

반응식

HRID 27007 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.[C:12]([C:17]1[CH2:18][S:19][CH2:20][CH2:21][N:22]=1)(OCC)=[O:13].CCCCCC>CCOCC.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:17]3=[CH:18][S:19][CH2:20][CH2:21][N:22]3[C:9]2=[O:10])=[C:4]([F:11])[CH:3]=1

참가 물질

6

반응물 3

HCID 8058HexaneHCID 45582034-Chloro-2-fluorophenyl isocyanateHCID 213030583-Carbethoxy-5,6-dihydro-1,4-thiazine

생성물 1

HCID 233433902-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione수율 66.8%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 8.6 g of 4-chloro-2-fluorophenylisocyanate in 20 ml of anhydrous ether was added dropwise to a mixture of 9.8 g of crude 3-carbethoxy-5,6-dihydro-1,4-thiazine and 10 drops of triethylamine in 20 ml of ether. After the addition, 30 ml of hexane was added dropwise in 20 min. The solution was stirred at room temperature for 3 hrs. The solution was concentrated in vacuo to remove solvent. The resulting oil was crystallized from ether to give 10 g of 2-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione, m.p. 117.5°-120.5° C.

후처리

  1. additionwas added dropwise in 20 min
  2. concentrationThe solution was concentrated in vacuo
  3. customto remove solvent
  4. customThe resulting oil was crystallized from ether

출처 및 근거

ORD 기록
ord-717bfbb6b90c4d1aae73fb1d40032188
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220465

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