Ethyl chloroformate → HCID 178473422, compound

HRID 1089725Notes

Reaction equation

HRID 1089725 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([OH:14])=[N:5]2.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>[OH-].[Na+].Cl>[Cl:12][C:11]1[CH:10]=[C:9]2[C:4](=[CH:3][C:2]=1[NH:1][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:5]=[C:6]([OH:14])[C:7]([OH:13])=[N:8]2

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 178507221HCID 178507221, compound

Product 1

HCID 178473422HCID 178473422, compoundYield 9,792.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 10 g (47,3 mmol) 6-amino-7-chloro-2,3-dihydroxyquinoxaline in 200 ml 0,5N sodium hydroxide was ice-cooled, and then 30 ml (0,36 mmol) ethyl chloroformate was added. Stirring was continued at 0° C. for 1 h and at 25° C. for 1 h. To the reaction mixture was added IN hydrochloric acid to pH 2-3, and the precipitated product was filtered off and washed with water to give 12 g of a crude product. Recrystallization (dimethylsulfoxide-0,5N hydrochloric acid) gave 10 g (75%) 6-chloro-7-ethoxycarbonylamino-2,3-dihydroxyquinoxaline, m.p.>300° C. NMR (DMSO-d 6):11.9 (2H, broad s), 8.9 (lH, broad s), 7.37 (lH,s), 7.17 (lH,s), 4.1 (2H,q), 1.28 (3H,t).

Workup

  1. temperaturecooled
  2. filtrationthe precipitated product was filtered off
  3. washwashed with water
  4. customto give 12 g of a crude product
  5. customRecrystallization (dimethylsulfoxide-0,5N hydrochloric acid)

Sources & evidence

ORD record
ord-5c6e213eba2c4646b95a32011cce29fb
Source dataset
uspto-grants-1992_01
Patent number
US05079250

Reaction notes

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