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

HRID 1381714ノート

反応式

HRID 1381714 の反応式
[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]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 5462222PotassiumHCID 14294241HCID 14294241、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e23cda9cbd564287a057d2ad2b668662
出典データセット
uspto-grants-1989_02
特許番号
US04803280

反応ノート

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