3-Chloroaniline → Methanimidamide, N'-(3-chlorophenyl)-N,N-dimethyl-

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[CH3:11][N:12]([CH:14]=[N:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=1)[CH3:13]

Participants

Reactant 2

HCID 79323-Chloroaniline

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 415383Methanimidamide, N'-(3-chlorophenyl)-N,N-dimethyl-Yield 100.5%

Procedure

A mixture of 3-chloroaniline (63.8 g, 0.50 mol) and dimethylformamide dimethyl acetal (106 ml, 0.75 mol) was heated at 100° for 2 h and evaporated at 60° at 0.5 mm Hg to give 91.8 g amber oil; ms 183.0 (M+H)+.

Workup

temperaturewas heated at 100° for 2 h
customevaporated at 60° at 0.5 mm Hg

Sources & evidence

ORD record: ord-39ce25f3d8bb4aeda4ce9dd1583f6e98
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE042376E1

Reaction notes

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