Hydrochloric Acid → HCID 21107906, compound

HRID 1765962Notes

Reaction equation

[C:1]1([C:7]2[C:8]([NH2:20])=[C:9]([NH2:19])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](O)(=O)[CH:22]([CH3:24])[OH:23].Cl>>[C:13]1([C:10]2[C:9]3[N:19]=[C:21]([CH:22]([OH:23])[CH3:24])[NH:20][C:8]=3[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 612Lactic Acid

HCID 22642269[1~1~,2~1~:2~4~,3~1~-Terphenyl]-2~2~,2~3~-diamine

Product 1

HCID 21107906HCID 21107906, compoundYield 82.8%

Conditions

Temperature: 140 °C

Procedure

A mixture of 1.25 g (4.8 mmol) 1,1′:4′,1″-terphenyl-2′,3′-diamine, 0.75 ml (8.6 mmol) 85% aq. lactic acid and 4.8 ml 4N HCl were stirred at reflux for 6 hours and then the volatile materials evaporated over 1 hour. The oily residue was heated to 140° C. and stirred for 15 min. After cooling to room temperature 10 ml water were added and the mixture triturated for 30 min. Addition of conc. NH4OH to pH˜7.5–8 followed by filtration, washing with water (4×10 ml) and drying under vacuum at 60° C. gave 1.25 g (82.8%) of the desired product. 1H NMR (250 MHz, CDCl3), δ, ppm: 1.58 (d, JHH=6.7 Hz, 3H), 3.64 (br.s, 1H), 5.07 (q, 1H), 7.37–7.76 (m, 12 H), 9.53 (br. s, 1H).

Workup

temperatureat reflux for 6 hours
customthe volatile materials evaporated over 1 hour
stirringstirred for 15 min
temperatureAfter cooling to room temperature 10 ml water
additionwere added
customthe mixture triturated for 30 min
additionAddition of conc. NH4OH to pH˜7.5–8
filtrationfollowed by filtration
washwashing with water (4×10 ml)
customdrying under vacuum at 60° C.

Sources & evidence

ORD record: ord-76c37df206514dbaa5dd3d8a53a66a9f
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229943B2

Reaction notes

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