Hexane → HCID 19784798, compound

HRID 257244Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[CH2:3][C:4]1(N)[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]1[N+:11]([O-:13])=[O:12].Cl[C:18]([O:20][CH2:21][CH2:22][Cl:23])=[O:19].CCCCCC>O1CCOCC1>[Cl:23][CH2:22][CH2:21][O:20][C:18](=[O:19])[NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]([F:16])([F:15])[F:1])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N1 -(2,2,2,-trifluoroethyl)-2-nitro-p-phenylene-diamine (6) (0.705 g, 3 mmol), 2-chloroethyl chloroformate (0.515 g, 3.6 mmol) and CaCo3 (0.40 g, 4 mmol) in dioxane (10 ml) was stirred at 80° C. for 20 minutes, filtered and washed with ethyl acetate. The combined filtrate was washed with water and brine, dried (Na2SO4), and evaporated to give a brown oil. Trituration with hexane gave 2-chloroethyl-N-[4-(2,2,2-trifluoroethyl)-3-nitrophenyl]-carbamate (8) as an orange solid. The unpurified carbamate (8) was dissolved in aqueous ethanol (ETOH: H2O, 15/5 ml) and powdered KOH (1.35 g) was added. The mixture was stirred at 90° C. for 20 minutes and then poured onto crushed ice (20 g) . The resultant mixture was extracted with ethyl acetate, washed with water and brine, dried (Na2SO4), and evaporated to give 0.544 g (65% yield) of N1 -(2,2,2-trifluoroethyl)-N4 -(2-hydroxyethyl)-2-nitro-p-phenylenediamine (9): mp 93°-95° C.; MS m/e 279(M+); 1HNMR (acetone-d6), δ3.25 (m, 2H), 3.76 (m, 2H), 3.91 (bs, 1H), 4.34 (m, 2H), 4.98 (bs, 1H), 7.19 (m, 2H), 7.35 (s,1H), 7.80 (bs, 1H).

Workup

filtrationfiltered
washwashed with ethyl acetate
washThe combined filtrate was washed with water and brine
dry with materialdried (Na2SO4)
customevaporated
customto give a brown oil

Sources & evidence

ORD record: ord-d153aeb06e594dae95d5f2cd8e030a42
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05260488

Reaction notes

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