Ethyl chloroformate → HCID 18606997, compound

HRID 1906407Notes

Reaction equation

HRID 1906407 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.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>N1C=CC=CC=1>[CH2:35]([O:34][C:32]([O:1][C@@H:2]1[C@H:8]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=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)=[O:33])[CH3:36]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 13823438HCID 13823438, compound

Product 1

HCID 18606997HCID 18606997, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.8 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 10 mL of pyridine (dried over potassiuwm hydroxide) in an ice-bath, 0.4 g of ethyl chloroformate was added dropwise then stored in the freezer overnight. The mixture was concentrated under reduced pressure and the residue was partitioned between ether and dilute sodium hydroxide. The ether solution was washed with brine then dried (magnesium sulfate) and removal of the solvent gave 0.9 g (97%) of (±)-cis-3-[(ethoxycarbonyl)oxy]-2,3-dihydro-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one. A sample was crystallized from ether--pet. ether, mp 168°-169°.

Workup

  1. customthen stored in the freezer overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between ether and dilute sodium hydroxide
  4. washThe ether solution was washed with brine
  5. customthen dried
  6. custom(magnesium sulfate) and removal of the solvent

Sources & evidence

ORD record
ord-3556b48a01f34cac944103814f111f21
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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