O-Phenylenediamine → HCID 19591898, compound

HRID 1601052Notes

Reaction equation

HRID 1601052 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([N:16]([CH2:18][C:19](O)=[O:20])[CH3:17])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C(Cl)Cl>[C:12]([O:11][C:9]([N:16]([CH2:18][C:19]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH2:8])=[O:20])[CH3:17])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

Product 1

HCID 19591898HCID 19591898, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of phenylenediamine (100 g, 0.924 mole) and Boc-sarcosine (175 g, 0.924 mole) in DMF (1750 mL) was cooled to -10° C. under argon, and a solution of DCC (190.8 g, 0.924 mole) in CH2Cl2 (1750 mL) was added in a slow stream over 1 hr. The temperature rose to 0° C. during the addition. The reaction was stirred overnight while the temperature was allowed to rise to RT. The white precipitate was removed by filtration, and the filtrate was diluted with H2O (3.5 L) and saturated brine (1 L). The CH2Cl2 layer was separated and the aqueous phase was extracted with EtOAc (2×1 L). The combined organic layers were washed with H2O (1 L) and brine (0.5 L), then were concentrated to a yellow residue (341 g). This was triturated with EtOAc to afford the title compound (179.4 g, 70%): mp 134-136° C.

Workup

  1. additionThe temperature rose to 0° C. during the addition
  2. customto rise to RT
  3. customThe white precipitate was removed by filtration
  4. additionthe filtrate was diluted with H2O (3.5 L) and saturated brine (1 L)
  5. customThe CH2Cl2 layer was separated
  6. extractionthe aqueous phase was extracted with EtOAc (2×1 L)
  7. washThe combined organic layers were washed with H2O (1 L) and brine (0.5 L)
  8. concentrationwere concentrated to a yellow residue (341 g)
  9. customThis was triturated with EtOAc

Sources & evidence

ORD record
ord-31d8437c65dd425eab40c4f7f188d207
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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