Aniline → 10258-71-6

HRID 1796337Notes

Reaction equation

HRID 1796337 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(CC)CC.[N-:20]=[N+:21]=[N-:22].[Na+]>ClCCl.CN(C=O)C.C(OCC)(=O)C>[C:7]1([NH:6][C:3](=[O:4])[CH2:2][N:20]=[N+:21]=[N-:22])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 33557Sodium Azide

Product 1

HCID 1420110110258-71-6Yield 63.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetyl chloride (5.1 ml, 64.5 mmol) was added drop wise to a solution of aniline (5 g, 53.7 mmol) and Et3N (18.7 ml, 134.3 mmol) in dichloromethane (150 ml) at 0° C. under argon. After the completion of reaction (TLC control), the reaction mixture was diluted with dichloromethane (300 ml). The resultant mixture was washed with water, brine and dried. The residue obtained upon evaporation of solvent was taken up in dry DMF (40 ml), added NaN3 (6.15 g, 94.6 mmol) and the resultant mixture was stirred at 80° C. for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water, brine and dried. The residue obtained upon evaporation of the solvent was chromatographed over silica gel to afford the azide (6 g, 63%).

Workup

  1. customAfter the completion of reaction (TLC control)
  2. washThe resultant mixture was washed with water, brine
  3. customdried
  4. customThe residue obtained upon evaporation of solvent
  5. washwashed with water, brine
  6. customdried
  7. customThe residue obtained upon evaporation of the solvent
  8. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-6a700076c287494c8d03536b6079b70d
Source dataset
uspto-grants-2006_04
Patent number
US07030148B2

Reaction notes

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