Dichloromethane → HCID 13732399, compound

HRID 648482Notes

Reaction equation

HRID 648482 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C(=O)([O-])O.[Na+].ClCCl>O>[C:16]([NH:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 20025775HCID 20025775, compound

Product 1

HCID 13732399HCID 13732399, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.7 parts of ethyl 2-[(4-aminophenyl)amino]acetate hydrochloride, 1.1 parts of acetic acid anhydride, 0.98 parts of sodium hydrogen carbonate, 65 parts of dichloromethane and 50 parts of water was stirred for 30 minutes at room temperature. The organic phase was separated, washed with water, dried, filtered and evaporated. The residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane, yielding 1.9 parts (68%) of ethyl 2-[[4-(acetylamino)phenyl]amino]acetate; mp. 119.5° C. (12).

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-8cdfcaf324964638a64de2c895b5524e
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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