Thionyl Chloride → HCID 19020448, compound

HRID 1087559Notes

Reaction equation

HRID 1087559 reaction equation
O=[C:2]1[N:7]2[CH2:8][CH2:9][S:10](=O)[C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:6]2=[C:5]([C:17]([O:19][CH3:20])=[O:18])[CH:4]=[C:3]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(Cl)([Cl:29])=O>>[Cl:29][CH:9]1[CH2:8][N:7]2[CH2:2][C:3]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:4][C:5]([C:17]([O:19][CH3:20])=[O:18])=[C:6]2[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[S:10]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14666681HCID 14666681, compound

Product 1

HCID 19020448HCID 19020448, compound

Procedure

aa) 15.7 g of methyl 5,6-dihydro-8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepine-11-carboxylate 4-oxide were added portionwise to 70 ml of thionyl chloride with the exclusion of moisture in such a manner that the temperature of the reaction solution is at about 35°. After completion of the addition, the mixture was stirred until the reaction was completed. The excess thionyl chloride was removed in vacuo and the residue was treated with 100 ml of water. The crystals were removed by filtration and dried, whereupon they were chromatographed on silica gel. By recrystallization from toluene, there was obtained methyl 5-chloro-5,6-dihydro-9-phenyl8H-pyrido[1,2-d]thieno-[2,3-f][1,4]thiazepin-11-carboxylate as yellow crystals of m.p. 192°-196°.

Workup

  1. customis at about 35°
  2. additionAfter completion of the addition
  3. customThe excess thionyl chloride was removed in vacuo
  4. additionthe residue was treated with 100 ml of water
  5. customThe crystals were removed by filtration
  6. customdried, whereupon they
  7. customwere chromatographed on silica gel
  8. customBy recrystallization from toluene

Sources & evidence

ORD record
ord-0f836de270074c9f8c22f72ee449a63e
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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