2,4-Dichloro-6-methylbenzylamine → HCID 10735962, compound

HRID 963451Notes

Reaction equation

HRID 963451 reaction equation
C(O[C:4]1[C:5](=[O:14])[C:6](=[O:13])[C:7]=1[NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])C.[Cl:15][C:16]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([CH3:25])[C:17]=1[CH2:18][NH2:19]>C(O)C>[C:9]([NH:8][C:7]1[C:6](=[O:13])[C:5](=[O:14])[C:4]=1[NH:19][CH2:18][C:17]1[C:20]([CH3:25])=[CH:21][C:22]([Cl:24])=[CH:23][C:16]=1[Cl:15])([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 28009712,4-Dichloro-6-methylbenzylamineHCID 19082433HCID 19082433, compound

Product 1

HCID 10735962HCID 10735962, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound was prepared in a procedure similar to the one described in Example 4. From 3-ethoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione (0.22 g, 1.1 mmol) and 2,4-dichloro-6-methylbenzylamine (0.22 g, 1.2 mmol, containing approximately 5% of a compound which is regioisomeric with respect to the substitution on the aryl ring) in absolute ethanol (5.5 mL) there was obtained 0.34 g (89%) of 3-tert-butylamino-4-(2,4-dichloro-6-methyl-benzylamino)-cyclobut-3-ene-1,2-dione as a white solid, which contains approximately 5% of a compound which is regioisomeric with respect to substitution on the aryl ring: mp 264°-268° C.; 1H NMR (DMSO-d6) δ 7.54 (d, 1H), 7.46 (s, 1H), 7.43 (br t, 1H), 7.39 (d, 1H), 4.89 (d, 2H), 4.72 (d, minor isomer), 2.40 (s, 3H), 2.31 (s, minor isomer), 1.34 (s, 9H) ppm. IR (KBr): 3200, 2950, 1800, 1650 cm-1 ; MS (m/z) 340/342/344 (M+).

Workup

  1. customThis compound was prepared in a procedure similar to the one

Sources & evidence

ORD record
ord-331f90baefb34627a69419ce98c15e5b
Source dataset
uspto-grants-1998_06
Patent number
US05763474

Reaction notes

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