Phenethylamine → HCID 23797016, compound

HRID 2375936Notes

Reaction equation

HRID 2375936 reaction equation
CN(C)[CH2:3][CH2:4][NH:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1.C(N)C[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[N+:15]([C:13]1[CH:12]=[CH:11][C:9]2[N:10]=[C:6]([NH:5][CH2:4][CH2:3][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:7][C:8]=2[CH:14]=1)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 56724837HCID 56724837, compound

Product 1

HCID 23797016HCID 23797016, compound

Procedure

The title compound was prepared following the procedure for N,N-dimethyl-N′-(6-nitrobenzothiazol-2-yl)-ethane-1,2-diamine, using 4 eq of phenethylamine. Modified workup: Solid that had precipitated during course of reaction (amine salt) was filtered; no aqueous workup was conducted. 1H NMR (400 MHz, CDCl3): δ=3.03 (t, J=6.4 Hz, 3H), 3.77 (q, J=6.4 Hz, 2H), 7.23-7.30 (m, 3H), 7.33-7.38 (m, 2H), 7.52 (d, J=8.8 Hz, 1H), 8.21 (dd, J=8.8, 2.4 Hz, 1H), 8.51 (d, J=2.4 Hz, 1H). MS (ES+): m/z 300.10 [MH+]. HPLC: tR=3.57 min (ZQ2000, polar—5 min).

Workup

  1. customModified workup: Solid that had precipitated during course of reaction (amine salt)
  2. filtrationwas filtered
  3. customHPLC: tR=3.57 min (ZQ2000, polar—5 min)

Sources & evidence

ORD record
ord-4e6bc34c0fd74c47adbd55d80bbdd78a
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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