Ethyl Acetate → 1-Benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-urea

HRID 80182

反応式

HRID 80182 の反応式
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[S:13]1[C:17]2[CH:18]=[C:19]([NH2:22])[CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1.[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH2:27].C(OC(=O)C)C>C1COCC1.CCCCCC>[S:13]1[C:17]2[CH:18]=[C:19]([NH:22][C:2]([NH:27][CH2:26][CH:25]([O:28][CH3:29])[O:24][CH3:23])=[O:4])[CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 682886-AminobenzothiazoleHCID 89728Aminoacetaldehyde dimethyl acetalHCID 94429Triphosgene

生成物 1

HCID 687854451-Benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-urea収率 228.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

TEA (185 mL, 1.3315 mmol) and triphosgene (138 mg, 0.4660 mmol) were added to a solution of benzothiazol-6-ylamine (200 mg, 1.3315 mmol) in THF (20 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours. This was followed by the addition of 2,2-dimethoxy-ethylamine (173 mL, 1.5978 mmol) in THF and TEA (185 mL, 1.3315 mmol) and the stirring was continued for a further 18 hours at room temperature. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was concentrated and the concentrate was partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (100% ethylacetate) afforded 300 mg of 1-Benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-urea (80.21% yield).

後処理

  1. waitthe stirring was continued for a further 18 hours at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrate was partitioned between ethylacetate and water
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (100% ethylacetate)

出典と根拠

ORDレコード
ord-fa3dd9ed285e48509a13759cf84a641d
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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