Dichloromethane → HCID 17819319, compound

HRID 1956710Notes

Reaction equation

HRID 1956710 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[CH2:4][NH:5][C:6]1[C:7](=O)[C:8](=[O:13])[C:9]=1[O:10]CC.ClCCl.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([NH:27][C:7]1[C:8](=[O:13])[C:9](=[O:10])[C:6]=1[NH:5][CH2:4][C:3]1[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:2]=1[Cl:1])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 17819311HCID 17819311, compound

Product 1

HCID 17819319HCID 17819319, compound

Procedure

A mixture of 3,4-diethoxy-3-cyclobutene-1,2-dione (5 g, 29 mmol) and 2-chloro-6-methylbenzylamine (4.57 g, 29 mmol) in absolute ethanol (147 mL) was allowed to stand at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure and suspended in dichloromethane (200 mL). The slurry was stirred at room temperature for 18 hours, filtered, rinsed with dichloromethane, and concentrated under reduced pressure to give 6.42 g (78%) of a solid. A portion of this solid, 3-(2-chloro-6-methyl-benzylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione, (0.4 g, 1.43 mmol) was placed in t-butylamine (4 mL) and dichloromethane (4 mL) and allowed to stand at room temperature for 6 days. The solid was filtered, rinsed several times with ethyl acetate, and dried. This gave 0.31 g (71%) of the title compound as a white solid: mp 254°-257° C.; 1H NMR (DMSO-d6) δ7.46 (br s, 1H), 7.42 (br t, 1H), 7.38-7.22 (m, 3H), 4.93 (d, 2H), 2.40 (s, 3H), 1.34 (s, 9H) ppm. IR (KBr): 3200, 2960, 1790, 1650 cm-1 ; MS (m/z) 306/308 (M+).

Workup

  1. filtrationThe solid was filtered
  2. washrinsed several times with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-c89da459f908483fa24cb011bee82517
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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