Hydrochloric Acid → HCID 20375534、化合物

HRID 1448792ノート

反応式

HRID 1448792 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][C:5]2=[CH:9][S:10][CH:11]=[C:4]2[S:3]1(=[O:13])=[O:12].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23].C(N(CC)CC)C.Cl>CS(C)=O>[OH:8][C:7]1[N:2]([CH3:1])[S:3](=[O:13])(=[O:12])[C:4]2[C:5](=[CH:9][S:10][CH:11]=2)[C:6]=1[C:22](=[O:23])[NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76833Chlorophenyl isocyanateHCID 16638702HCID 16638702、化合物

生成物 1

HCID 20375534HCID 20375534、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

1 g (4.6 mmol) of 3,4-dihydro-2-methyl-3-oxo-2H-thieno[3,4]-1,2-thiazine 1,1-dioxide are stirred at room temperature for 3 hours under nitrogen with 0.71 g (4.6 mmol) of o-chlorophenylisocyanate and 0.47 g (4.6 mmol) of triethylamine in 10 ml of absolute dimethylsulfoxide. Thereafter, the mixture is poured into 40 ml of 2-N hydrochloric acid and 25 g of ice and stirred for 20 minutes. The separated precipitate is filtered off under suction and washed neutral with water. The precipitate is dissolved in 200 ml of methylene chloride, the turbid solution is dried over sodium sulfate, stirred with 0.3 g of active carbon and filtered. The filtrate is extracted with five 100 ml portions of saturated sodium carbonate solution, each of the aqueous phases being re-extracted with a small amount of methylene chloride. The combined aqueous phases are acidified to pH 1 with concentrated hydrochloric acid. The separated product is extracted with two 150 ml portions of methylene chloride. The combined organic phases are dried over sodium sulfate. The solvent is distilled off, whereby the product crystallizes out. For purification, the product is recrystallized from ca 30 ml of methanol. There is obtained 3-hydroxy-2-methyl-4-(2-chlorophenylcarbamoyl)-2H-thieno[3,4-e]-1,2-thiazine 1,1-dioxide of melting point 152°-155° C.

後処理

  1. filtrationThe separated precipitate is filtered off under suction
  2. washwashed neutral with water
  3. dissolutionThe precipitate is dissolved in 200 ml of methylene chloride
  4. dry with materialthe turbid solution is dried over sodium sulfate
  5. stirringstirred with 0.3 g of active carbon
  6. filtrationfiltered
  7. extractionThe filtrate is extracted with five 100 ml portions of saturated sodium carbonate solution
  8. extractioneach of the aqueous phases being re-extracted with a small amount of methylene chloride
  9. extractionThe separated product is extracted with two 150 ml portions of methylene chloride
  10. dry with materialThe combined organic phases are dried over sodium sulfate
  11. distillationThe solvent is distilled off
  12. customwhereby the product crystallizes out
  13. customFor purification
  14. customthe product is recrystallized from ca 30 ml of methanol

出典と根拠

ORDレコード
ord-66bbee2e42fd4cd2982a48c6ac75f890
出典データセット
uspto-grants-1980_02
特許番号
US04187303

反応ノート

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