1-Chloro-2-(chloromethoxy)ethane → HCID 135415636, compound

HRID 2417222Notes

Reaction equation

C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:16]=[N:15][C:14]3[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]2=3)C=CC=CC=1.[Cl:31][CH2:32][CH2:33][O:34][CH2:35]Cl>CN(C=O)C>[Cl:31][CH2:32][CH2:33][O:34][CH2:35][N:15]1[C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]=2[N:8]=[CH:16]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 6 (1.77 g, 4.49 mmol) in DMF (30 mL) was added (2-chloroethoxy)methyl chloride (0.65 g, 5.0 mmol). The reaction mixture was stirred at 25° C. for 8.0 h. The solution was then partitioned between EtOAc (100 mL) and water (100 mL). The EtOAc solution was washed with water (4×100 mL); then it was dried over MgSO4 (s) and filtered. Evaporation under reduced pressure and purification of the residue by use of column chromatography (EtOAc) afforded 7 (1.07 g, 4.39 mmol) in 88%: mp>280° C. (dec.); Rf(hexanes/EtOAc=1:2) 0.20; UV (EtOH) λmax 288 (ε 15,100); 1H NMR (DMSO-d6) δ 3.67 (t, J=6.10 Hz, 2 H, CH2Cl), 3.75 (t, J=6.10 Hz, 2 H, OCH2), 5.62 (s, 2 H, H2C1′), 6.15 (s, 2 H, NH2), 7.58 (s, 1 H, NH), 8.16 (s, 1 H, HC8); 13C NMR (DMSO-d6) δ 43.39 (CH2Cl), 68.50 (OCH2) 74.71 (C1′), 107.71 (C5), 143.87 (C8), 153.15 (C4), 154.37 (C2), 159.12 (C6); MS m/z 243 (M+, Cl-cluster). Anal (C8H10ClN5O2) C, H, N, Cl; calcd (%): 39.43, 4.14, 28.74, 14.56; found (%): 39.38, 4.13, 28.70, 14.45.

Workup

customThe solution was then partitioned between EtOAc (100 mL) and water (100 mL)
washThe EtOAc solution was washed with water (4×100 mL)
dry with materialthen it was dried over MgSO4 (s)
filtrationfiltered
customEvaporation
customunder reduced pressure and purification of the residue by use of column chromatography (EtOAc)

Sources & evidence

ORD record: ord-f3c508833448403385c8c584cc096272
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825348B2

Reaction notes

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