3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine → N-[3-[3-[(Dimethylamino)methyl]phenoxy]propyl]-N'-[2-[[5-[(methylamino)methyl]-2-furanylmethyl]thio]ethyl]-2-nitro-1,1-ethenediamine

HRID 224650Notes

Reaction equation

HRID 224650 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[O:5][C:6]([CH2:9][S:10][CH2:11][CH2:12][NH:13][C:14](SC)=[CH:15][N+:16]([O-:18])=[O:17])=[CH:7][CH:8]=1.[NH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH2:32][N:33]([CH3:35])[CH3:34])[CH:29]=[CH:30][CH:31]=1>>[CH3:34][N:33]([CH2:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[O:25][CH2:24][CH2:23][CH2:22][NH:21][C:14]([NH:13][CH2:12][CH2:11][S:10][CH2:9][C:6]1[O:5][C:4]([CH2:3][NH:2][CH3:1])=[CH:8][CH:7]=1)=[CH:15][N+:16]([O-:18])=[O:17])[CH3:35]

Participants

3

Reactant 2

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineHCID 705383981-Nitro-2-methylthio-2-{2-[(5-methylaminomethyl-2-furyl)methylthio]ethylamino}ethylene

Product 1

HCID 70538242N-[3-[3-[(Dimethylamino)methyl]phenoxy]propyl]-N'-[2-[[5-[(methylamino)methyl]-2-furanylmethyl]thio]ethyl]-2-nitro-1,1-ethenediamine

Procedure

A mixture of N-methyl-5-[[[2-[(1-methylthio-2-nitroethenyl)amino]ethyl]thio]methyl]-2-furanmethanamine (1.6 g) (prepared from the oxalate salt) and 3-(3-aminopropoxy)-N,N-dimethylbenzenemethanamine (1.15 g) was heated at 98°-100° for 3 hours. The oily product was chromatographed (silica/methanol-0.88 ammonia 79:1) and the appropriate eluate evaporated to dryness to give the title compound as a hydrate as an amber oil (2.12 g).

Workup

  1. temperaturewas heated at 98°-100° for 3 hours
  2. customThe oily product was chromatographed (silica/methanol-0.88 ammonia 79:1)
  3. customthe appropriate eluate evaporated to dryness

Sources & evidence

ORD record
ord-4303ae74ac7842a8b3c04667c62708dd
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Reaction notes

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