Ammonia → HCID 19736731, compound

HRID 326306Notes

Reaction equation

HRID 326306 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([O:17][C:7]=2[C:6]([S:19](Cl)(=[O:21])=[O:20])=[C:5]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3.N.C([N:33](CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([O:17][C:7]=2[C:6]([S:19](=[O:21])(=[O:20])[NH2:33])=[C:5]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8471TriethylamineHCID 19736710HCID 19736710, compound

Product 1

HCID 19736731HCID 19736731, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 2-{(5-methoxy-8-chlorosulfonyl -3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,1'-cyclohexan]-7-yl)oxy}acetate (prepared in Preparation 70) (0.32 g, 0.74 mmol) in dichloromethane (4 ml) is added dropwise to a solution of liquid ammonia (2 ml, 80 mmol) and triethylamine (0.1 ml, 0.7 mmol) in dichloromethane (4 ml) at -25° to -20 ° C. After stirring at the same temperature for 30 minutes, the solvent is removed by distillation. The residue is placed on a silica gel column and eluted with a mixture of acetone and dichloromethane (1:1) to yield the title compound as a crystalline solid (0.173 g, yield 56.5%). Recrystallization from a mixture of ethyl acetate and ether gives a product having a melting point of 188°-190° C.

Workup

  1. customthe solvent is removed by distillation
  2. washeluted with a mixture of acetone and dichloromethane (1:1)

Sources & evidence

ORD record
ord-451b61b6ef46456eb3d2cf03c7c19b16
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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