Ethyl bromoacetate → [[5-[4-(1,1-Dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]acetic acid ethyl ester

HRID 1381714노트

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HRID 1381714 반응식
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][N:14]=[N:13][C:12]=2[SH:16])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[K].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][S:16][C:12]1[N:13]=[N:14][S:15][C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:10][CH:9]=1)[CH3:24]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 5462222PotassiumHCID 14294241HCID 14294241, 화합물

생성물 1

HCID 14294226[[5-[4-(1,1-Dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]acetic acid ethyl ester수율 83.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2.9 g of 5-[4-(1,1-dimethylethyl)phenyl]-1,2,3-thiadiazole-4-thiol, potassium salt in 50 ml of ethanol was stirred overnight with 1.67 g of ethyl bromoacetate, then concentrated in vacuo. The residue was taken up in ether, filtered and evaporated in vacuo. The oily residue was dissolved in dichloromethane and purified as described in Example 50, giving an oil which was crystallized from methylcyclohexane, giving 2.8 g of the desired compound as white needles, mp 62.5°-63.5° C. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 1.21 (t, 3H, J=7.0 Hz, CH3); 1.37 (s, 9H, t-butyl); 4.11 (s, 2H, SCH2); 4.15 (q, 2H, CH2O); 7.55 (s, 4H, C6H4). Infrared absorption spectrum (KBr pellet): 1739(s); 1606(w); 1520(w); 1480(w); 1445(w); 1385(w); 1365(w); 1305(s); 1175(s); 1040(w); 935(s); 840(s).

후처리

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. dissolutionThe oily residue was dissolved in dichloromethane
  5. custompurified
  6. customgiving an oil which
  7. customwas crystallized from methylcyclohexane

출처 및 근거

ORD 기록
ord-e23cda9cbd564287a057d2ad2b668662
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04803280

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