Cyclopropanecarbonyl chloride → HCID 18606996, compound

HRID 1906408Notes

Reaction equation

HRID 1906408 reaction equation
[OH:1][C@@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[N:4]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:3]1=[O:30])=[CH:21][CH:20]=[CH:19][CH:18]=3.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>N1C=CC=CC=1>[CH:31]1([C:34]([O:1][C@@H:2]2[C@H:8]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[S:7][C:6]3[C:17]4[C:22]([CH:23]=[CH:24][C:5]=3[N:4]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:3]2=[O:30])=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:35])[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 13823438HCID 13823438, compound

Product 1

HCID 18606996HCID 18606996, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.0 g of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one in 25 mL pyridine was added dropwise at ice-bath temperature 0.9 g of cyclopropanecarboxylic acid chloride and the solution was kept at this temperature for 17 hours. The mixture was concentrated and the residue, in water, was made basic with concentrated ammonium hydroxide. The aqueous suspension was extracted with ethyl acetate (3×60 mL). The combined ethyl acetate solutions were washed with brine and dried (magnesium sulfate). Removal of the solvent gave 2.3 g (100%) of (±)-cis-3-[(cyclopropylcarbonyl)oxy]-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one as an amorphous compound.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe aqueous suspension was extracted with ethyl acetate (3×60 mL)
  3. washThe combined ethyl acetate solutions were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-8267cb1f036a4b68bea43ab5ab70bc03
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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