3-Chloroaniline → HCID 9908998, compound

HRID 1108506Notes

Reaction equation

HRID 1108506 reaction equation
Cl.[C:2]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3].[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.CCOCC>CN(C=O)C.C(Cl)Cl.CCOC(C)=O.C(N(CC)CC)C>[ClH:21].[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:16](=[O:18])[CH2:15][CH2:14][C:13]2[N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:20][CH:19]=3)[CH:10]=[N:11][CH:12]=2)[CH:26]=[CH:27][CH:28]=1

Participants

10

Reactant 5

HCID 79323-ChloroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10953452Ether hydrochlorideHCID 70298542HCID 70298542, compound

Product 1

HCID 9908998HCID 9908998, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of acid 6 (141 mg) in 2 mL of dry DMF was added triethylamine (0.089 mL), and 3-chloroaniline (0.046 mL). 1-Hydroxybenzotriazole hydrate (80 mg) was added, followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (106 mg). After six hours, the reaction was poured into EtOAc, washed with sat. aq. NaHCO3 solution and brine, then dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by silica gel chromatography (2-6% MeOH/CH2Cl2) gave a white foam which was taken up in CH2Cl2, treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 1 was isolated as a white powder.

Workup

  1. washwashed with sat. aq. NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the crude product
  6. customPurification by silica gel chromatography (2-6% MeOH/CH2Cl2)
  7. customgave a white foam which
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1adb086b24c454c9d54b31adbc00131
Source dataset
uspto-grants-2000_05
Patent number
US06066738

Reaction notes

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