2,4-Dichlorobenzylamine → HCID 10617174, compound
Reaction equation
C(O[C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][CH:11]([CH3:15])[CH:12]([CH3:14])C)CCC.[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22].O1CCC[CH2:29]1>>[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:15])([CH3:29])[CH2:12][CH3:14]Participants
Procedure
A solution of 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (7.18 g, 30 mmol, Example 5) and 2,4-dichlorobenzylamine (5.28 g, 30 mmol) in tetrahydrofuran (40 mL) was stirred at room temperature for 16 hours. The solvent was removed and the residue was triturated thoroughly with diethyl ether and dried to give 8.94 g of a crude product. Successive recrystallizations of this material from acetonitrile (charcoal), acetonitrile (twice), acetone (charcoal) and acetone (twice) afforded 4.08 g (40%) of the title compound as a white, electrostatic solid: mp 196°-197° C. (softens 188° C.); 1H NMR (DMSO-d6): δ 7.81 (m, 1H), 7.68 (m, 1H), 7.48 (m, 3H), 4.81 (d, 2H), 1.67 (m, 2H), 1.31 (s, 6H), 0.82 (t, 3H) ppm. IR (KBr): 3210, 1790, 1645 cm-1 ; MS (m/z) 340/342/344 (M+). HPLC indicates a major component (99% ). Differential scanning calorimetry studies indicate that this material is a mixture of crystal forms.
Workup
- customThe solvent was removed
- customthe residue was triturated thoroughly with diethyl ether
- customdried
- customto give 8.94 g of a crude product
- customSuccessive recrystallizations of this material from acetonitrile (charcoal), acetonitrile (twice), acetone (charcoal) and acetone (twice)
Sources & evidence
- ORD record
- ord-3becbea2af56412a9088597a417f52be
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05763474
Reaction notes
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