Ammonia → (cis-4,5-Diphenyl-4,5-dihydro-1H-imidazol-2-yl)amine

HRID 18724Notes

Reaction equation

[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10](C(OC(C)(C)C)=O)[C:9](SC)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:27]>C(O)CO>[C:12]1([C@H:11]2[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:8][C:9]([NH2:10])=[N:27]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A solution of intermediate 59 (1.0 g, 2.71 mmol) in ethylene glycol (10 mL) is saturated with ammonia and is heated in a pressure tube at 115° C. for 3 h. The reaction mixture is cooled to rt, and saturated with ammonia, and heated is heated at 115° C. overnight. The reaction mixture is cooled to rt, and the product is precipitated by the addition of addition of water to give 226 mg of the product 122. 1H NMR (DMSO-d6) δ 7.10-6.80 (m, 10 H), 6.40 (bs, 3 H), 5.10 (s, 2 H); LC/MS: 2.89 min, m/z 238 (M++1).

Workup

temperatureThe reaction mixture is cooled to rt
temperatureis heated at 115° C. overnight
temperatureThe reaction mixture is cooled to rt
customthe product is precipitated by the addition of addition of water

Sources & evidence

ORD record: ord-2d62f557fbb243ceaea737eaf4f4f398
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741493B2

Reaction notes

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