1,4-Dibromo-2,2-diethoxy-3-butanone → HCID 178467676、化合物

HRID 280732

反応式

HRID 280732 の反応式
[Br:1][CH2:2][C:3]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[C:4](=O)[CH2:5]Br.[C:14]([NH:17][C:18]([NH2:20])=[S:19])(=[NH:16])[NH2:15]>O1CCCC1>[CH4:2].[NH:17]([C:18]1[S:19][CH:5]=[C:4]([C:3]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[CH2:2][Br:1])[N:20]=1)[C:14]([NH2:16])=[NH:15]

参加物

5

反応物 2

HCID 131009731,4-Dibromo-2,2-diethoxy-3-butanoneHCID 178513045HCID 178513045、化合物

生成物 2

HCID 297MethaneHCID 178467676HCID 178467676、化合物収率 71.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 25.5 g (80 mmol) of 1,4-dibromo-2,2-diethoxy-3-butanone, 11.8 g (100 mmol) of N-amidinothiourea, and 150 ml of tetrahydrofuran was heated at reflux for 3 hours. The mixture was filtered to remove some insoluble solid, and the filtrate was concentrated. The residue was triturated with 200 ml of saturated sodium bicarbonate, then extracted four times with a total of 500 ml of ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate, filtered and evaporated leaving a solid. Recrystallization from 250 ml of acetonitrile, after decolorization with charcoal, afforded 9.7 g (36%) of 2-guanidino-4-(2-bromo-1,1-diethoxyethyl)thiazole as a white solid, mp 157°-158°; calcd. for C10H17N4O2SBr: C, 35.62; H, 5.08; N, 16.61; Br, 23.69; S, 9.51; found: C, 35.60; H, 4.97; N, 16.99; Br, 23.75; S, 9.59.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. customto remove some insoluble solid
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with 200 ml of saturated sodium bicarbonate
  7. extractionextracted four times with a total of 500 ml of ethyl acetate
  8. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customleaving a solid
  12. customRecrystallization from 250 ml of acetonitrile

出典と根拠

ORDレコード
ord-f3ffcaeabb7f4ad9ac8cf42c953eed67
出典データセット
uspto-grants-1986_05
特許番号
US04590299

関連ノート

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