4-Bromobenzene-1,2-diamine → HCID 178478445, compound

HRID 1433186Notes

Reaction equation

HRID 1433186 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.Cl.C(O[C:14](=N)[CH2:15][Cl:16])C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:14]([CH2:15][Cl:16])=[N:9][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 3235934-Bromobenzene-1,2-diamineHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochloride

Product 1

HCID 178478445HCID 178478445, compound

Procedure

Using the procedure for Step D in Example 1 (as described in J. Med. Chem., 1986, 29, 2280), the title compound was prepared from 4-bromo-benzene-1,2-diamine (200 mg, 1.07 mmol) and 2-chloroacetimidic acid ethyl ester hydrochloride salt (168 mg, 1.07 mmol) and was obtained as an off-white solid (240.3 mg, 92% yield). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.75 (d, 1H, J=1.4 Hz), 7.47 (d, 1H, J=8.6 Hz), 7.74 (dd, 1H, J=8.6 Hz, J=1.3 Hz), 4.84 (s, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C18H20ClN3O2S: 247.50 (M+H), Found 247.0.

Sources & evidence

ORD record
ord-9881bb7f929646fa883268b24a8fb095
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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