Methyl chloroformate → HCID 9933099, compound

HRID 1377796Notes

Reaction equation

HRID 1377796 reaction equation
[NH2:1][CH2:2][C:3]1[C:16]2[S:15][C:14]3[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=3)[C:8](=[O:19])[C:7]=2[C:6]([NH:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH3:39])=[O:37]>C(Cl)(Cl)Cl>[CH2:26]([N:23]([CH2:24][CH3:25])[CH2:22][CH2:21][NH:20][C:6]1[C:7]2[C:8](=[O:19])[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([O:17][CH3:18])[CH:10]=3)[S:15][C:16]=2[C:3]([CH2:2][NH:1][C:36](=[O:37])[O:38][CH3:39])=[CH:4][CH:5]=1)[CH3:27]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 10596263HCID 10596263, compound

Product 1

HCID 9933099HCID 9933099, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.55 g of 4-(aminomethyl)-l-[[2-(diethylamino)ethyl]amino]-7-methoxythioxanthen-9-one in 40 mL of chloroform containing 2 mL of triethylamine chilled to 0° C. was added 0.45 mL of methyl chloroformate and the mixture was stirred at room temperature for several hours. The solvent was removed in vacuo, the residue was purified by flash chromatography (silica gel; eluting with chloroform, then 1% triethylamine in chloroform/hexane (1:1)) affording 1.2 g of methyl N-[[1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-yl]-methyl]carbamate which was recrystallized from ethyl acetate to yield 0.79 g of a bright yellow solid, m.p. 131°-132° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (silica gel
  3. washeluting with chloroform

Sources & evidence

ORD record
ord-e5a00254a85c42109f9ebead3c4466fc
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

Loading…