Triethylamine → 4-(2,4-dichlorophenyl)-5-methyl-2-[N-(alpha-cyclopropylbenzyl)-N-propylamino]thiazole

HRID 128692ノート

反応式

HRID 128692 の反応式
[CH:1]1([CH:4]([N:11]([CH2:15][CH2:16][CH3:17])[C:12]([NH2:14])=[S:13])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH:26]([CH3:37])[C:27]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[Cl:36])=O>C(O)C>[Cl:36][C:30]1[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:29]=1[C:27]1[N:14]=[C:12]([N:11]([CH:4]([CH:1]2[CH2:2][CH2:3]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:15][CH2:16][CH3:17])[S:13][C:26]=1[CH3:37]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-one2 回HCID 18967810N-(alpha-cyclopropylbenzyl)-N-propylthiourea2 回

生成物 1

HCID 193748934-(2,4-dichlorophenyl)-5-methyl-2-[N-(alpha-cyclopropylbenzyl)-N-propylamino]thiazole収率 79%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

To 1.35 g of N-(α-cyclopropylbenzyl)-N-propylthiourea (Compound 75) in 35 ml of ethanol, add 546 mg of triethylamine, then slowly 1.52 g of 2-bromo-1-(2,4-dichlorophenyl)-1-propanone (Compound 15). After 3 hours of heating at 75° C., remove the precipitate formed by filtration. The ethanolic solution is evaporated to dryness. Take up the residue in ethyl ether and wash with water until bromide ions have disappeared. Dry the organic phase over anhydrous sodium sulphate and then evaporate to dryness. Purify the residue on a silica column, using a mixture of cyclohexane and ethyl acetate (10:1 V/V) as eluent, to obtain the expected product. Recrystallise in acetonitrile (white crystals).

後処理

  1. customremove the precipitate
  2. customformed by filtration
  3. customThe ethanolic solution is evaporated to dryness
  4. washwash with water until bromide ions
  5. dry with materialDry the organic phase over anhydrous sodium sulphate
  6. customevaporate to dryness
  7. customPurify the residue on a silica column
  8. additiona mixture of cyclohexane and ethyl acetate (10:1 V/V) as eluent

出典と根拠

ORDレコード
ord-779b616a6258459bb0934ed8e5e45ab8
出典データセット
uspto-grants-1995_11
特許番号
US05464847

反応ノート

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