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

HRID 128692노트

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HRID 128692 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-one2회HCID 18967810N-(alpha-cyclopropylbenzyl)-N-propylthiourea2회

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-779b616a6258459bb0934ed8e5e45ab8
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464847

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