Chloroform → 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one

HRID 236154

Reaction equation

HRID 236154 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([S:7][C:8]2[C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:3]1.C(Cl)(Cl)[Cl:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:18][CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:14](=[O:16])[C:13]2[CH:12]=[CH:11][CH:10]=[N:9][C:8]=2[S:7]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 11776TriphenylphosphineHCID 137264322-[(1-Methyl-3-pyrrolidinyl)thio]-3-pyridinecarboxylic acid

Product 1

HCID 137264572-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 80.75 g (0.34 mole) of 2-[(1-methyl-3-pyrrolidinyl)thio]-3-pyridinecarboxylic acid, 500 ml of chloroform, 200 g of carbon tetrachloride and 178 g (0.68 mole) of triphenylphosphine was stirred at reflux for 2.5 hr. The resulting solution was extracted with one 500 ml and three 125 ml portions of 1N hydrochloric acid. The acid extracts were combined and extracted with isopropyl ether. The aqueous layer was basified with sodium hydroxide and extracted three times with chloroform. The combined chloroform extract was dried over sodium sulfate and concentrated. A portion of the residue was chromatographed on the high pressure liquid chromatograph using a silica column and ethyl acetate. The compound obtained was crystallized from isopropyl ether-isopropyl alcohol, m.p. 97°-100° C.

Workup

  1. temperatureat reflux for 2.5 hr
  2. extractionThe resulting solution was extracted with one 500 ml and three 125 ml portions of 1N hydrochloric acid
  3. extractionextracted with isopropyl ether
  4. extractionextracted three times with chloroform
  5. extractionThe combined chloroform extract
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated
  8. customA portion of the residue was chromatographed on the high pressure liquid chromatograph
  9. customThe compound obtained
  10. customwas crystallized from isopropyl ether-isopropyl alcohol, m.p. 97°-100° C.

Sources & evidence

ORD record
ord-5494095c5fd14bb5beabb3d84f851066
Source dataset
uspto-grants-1987_02
Patent number
US04642343

Linked notes

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