Chloroacetonitrile → HCID 59547214, compound

HRID 1097232Notes

Reaction equation

[Se-2:1].[Na+].[Na+].Cl[C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].Cl[CH2:14][C:15]#[N:16].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:8][C:7]1[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[Se:1][C:14]=1[C:15]#[N:16]

Participants

Conditions

Temperature: 105 °C

Procedure

To a suspension of sodium selenide (9.14 g, 72.6 mmol, prepared from 5.8 g of selenium as described above) in DMF (72 mL) was added a solution of 2-chlorobenzonitrile (10 g, 72.6 mmol) in DMF (25 mL) at rt for 5 min and stirred the mixture at 100-110° C. for 24 h. Then chloroacetonitrile (5.48 mL, 72.6 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (3.9 g, 72.6 mmol) in dry methanol (24 mL) was added dropwise and stirring was continued for 2 h at the same temperature. The mixture was allowed to room temperature (rt) and poured into cold water and stirred for 30 min. The precipitated solid was filtered, washed with water and dried to give the product as an off-white color solid (7 g, 44%), mp 158-160° C. 1H NMR (400 MHz, CDCl3): δ 7.76-7.79 (1H, m, H-7), 7.60-7.63 (1H, m, H-4), 7.41-7.52 (2H, m, H-5,6), 4.90 (2H, br s, —NH2).

Workup

stirringagain stirred at 60-70° C. for 2 h
stirringstirring
waitwas continued for 2 h at the same temperature
customwas allowed to room temperature
custom(rt)
stirringstirred for 30 min
filtrationThe precipitated solid was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-4b1804d194cf4748a7121e9900131e9c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143237B2

Reaction notes

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