1,1'-Thiocarbonyldiimidazole → 4-(4-Isothio-cyanatophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester

HRID 10783

반응식

HRID 10783 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22]>CN(C)C=O>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)=[C:21]=[S:22]

참가 물질

4

반응물 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

생성물 1

HCID 185218234-(4-Isothio-cyanatophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester수율 104.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 4-(4-aminophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (15 g, 54.1 mmol) (from Step B above) in N,N-dimethylformamide (120 mL) was added dropwise to a cooled (−15° C.) solution of 1,1′-thiocarbonyldiimidazole (9.66 g, 54.2 mmol) (Aldrich) in N,N-dimethylformamide (40 mL). After the addition was complete, the cooling bath was removed and the solution was stirred for 1 h. The mixture was poured into ice-water (1 L), stirred for 30 minutes, and extracted with diethyl ether. The combined extracts were dried over Na2SO4, and evaporated in vacuo to provide 4-(4-isothio-cyanatophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (18 g, 94%).

후처리

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. additionThe mixture was poured into ice-water (1 L)
  4. stirringstirred for 30 minutes
  5. extractionextracted with diethyl ether
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-66c9ae911dbb4a32a0ac6929b789a6cc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094896B2

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