Hydrochloric Acid → 2-(2,4-Dichloro-3-thienylamino)-1H-thieno[3,4-d]imidazole hydrochloride

HRID 349433

反応式

HRID 349433 の反応式
C1(C)C=CC(S([Cl:10])(=O)=O)=CC=1.[NH2:12][C:13]1[C:14]([NH:18][C:19]([NH:21][C:22]2[C:26]([Cl:27])=[CH:25][S:24][C:23]=2[Cl:28])=S)=[CH:15][S:16][CH:17]=1.[OH-].[Na+].Cl>C1COCC1.O.C(OCC)(=O)C>[ClH:10].[Cl:28][C:23]1[S:24][CH:25]=[C:26]([Cl:27])[C:22]=1[NH:21][C:19]1[NH:18][C:14]2=[CH:15][S:16][CH:17]=[C:13]2[N:12]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 86037752N-(4-Amino-3-thienyl)-N'-(2,4-dichloro-3-thienyl)thiourea

生成物 1

HCID 695138912-(2,4-Dichloro-3-thienylamino)-1H-thieno[3,4-d]imidazole hydrochloride

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 108.4 mg of p-toluenesulfonyl chloride in 5 ml of anhydrous THF was added dropwise to a mixture prepared from a solution of 157 mg of N-(4-amino-3-thienyl)-N′-(2,4-dichlorothienyl)thiourea in 15 ml of THF and a solution of 51.08 mg of NaOH in 2 ml of water. The resulting dark solution was stirred at room temperature for 2 hours, the solvent was distilled off and the residue was admixed with water. After extraction with ethyl acetate, the organic phase was washed with water and dried over sodium sulfate. After the solvent had been distilled off, the residue was purified by column chromatography on silica gel using a mixture of 20 parts by volume of ethyl acetate, 10 parts by volume of n-heptane, 3 parts by volume of glacial acetic acid as an eluent, which was then distilled off under reduced pressure. A viscous amorphous product was obtained which was dissolved in ethyl acetate and made strongly acidic using hydrogen chloride gas-saturated diethyl ether. The crystallization of the amorphous hydrochloric acid salt was brought about by scratching. M.p.: >300° C.

後処理

  1. distillationthe solvent was distilled off
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationAfter the solvent had been distilled off
  6. customthe residue was purified by column chromatography on silica gel using
  7. additiona mixture of 20 parts by volume of ethyl acetate, 10 parts by volume of n-heptane, 3 parts by volume of glacial acetic acid as an eluent
  8. distillationwhich was then distilled off under reduced pressure
  9. customA viscous amorphous product was obtained which
  10. customThe crystallization of the amorphous hydrochloric acid salt

出典と根拠

ORDレコード
ord-981a9008d2944f699921517f681de425
出典データセット
uspto-grants-2007_02
特許番号
US07179830B2

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