SU1214671A1 - Method of producing 5-amino-2,4-dicyano-2,3-dihydrofurans - Google Patents

Description

one

The invention relates to a new process for the preparation of new compounds, namely, 5-amino-2,4-dicyano--2,3-dihydrofurans, which can be used in organic synthesis.

The aim of the invention is the synthesis of new derivatives: aminonitrile 2,3-dihydrofurans, which can be used in the synthesis of biologically active compounds.

Example 1. 5-Amino-2,3-dimethyl 2,4-dicyano-2,3-dihydrofuran, 6 g (0.06 mol) of KHCO are added to 30 ml of water, then 10 g are slowly added 4. 4,5,5-Tetra-c-3-methyl-2-panto to dissolve i Then 5 g of a 30% hydrogen peroxide solution is added dropwise over 10 minutes while cooling the reaction mass at a rate such that the temperature of the reaction mass did not exceed 40-45 ° C. The precipitated product was filtered off, a saturated solution of NaCl was added to the filtrate to completely isolate the product, the Cristallic products were filtered out, combined and risotalysis from isopropanol. This gives 4.6 g (57%) of the desired product.

m.p. ne-in c.

Found,%: C 58, H 5.29; N 26.03

C, 0.

Calculated,%: C 58.89; H 5.52; N 25.77.

Example 2. 5-A {ino-2-ethyl -2,4-dicyano-2,3-dihydrofuran.

Analogously to Example 1, out of 10 g (0.05 mol) of 5,5,6,6-tetracyanohexanone-2, 3.9 g (48%) of the product with m.p. 130-131 ° C.

Found,%: C 59.08; H 5.31; N 25.49

CgH, N, 0,

Calculated,%: C 58.89; H 5.52; N 25.77.

Editor L. Castran

Compiled by T, Cascina Techred A, Ah

Order 852/34 Circulation 379Subscription

VNIIPI USSR State Committee for Inventions and Discoveries 4/5, Moscow, Zh-35, Raushsk nab. 113035

Branch ShSh Patent, Uzhgorod, Proektna str., 4

12146712

Example 3. 5-Amino-2,3 (trimethylene) -2,4-dicyano-2,3-dihydrofuran.

Analogously to Example 1, from 10.6 g of 5 (0.05 mol) of 2- (1,1,2,2) -tetracyano-cyclopentanone, 6.92 g (79%) of the product with m.p. 141-142 C.

Found,%: C 61.96; H 4.93; N 23.80.

C, H, N, 0,

Calculated,%: C61.71; H5.4; . N 24.00.

Example 4. 5-Amino-2,3 (tetramethylene) 2,4-dicyano-2,3-dihydrofuran.

Analogously to example 1, out of 11.3 g (0.05 mol) of 2- (1,1,2,2) -cyclohexanone, 5.1 g (54%) of the product was obtained with m.p. 142-143 ° C.

Found,%: C 63.71; H 5.63; S 22.0

C ,, H ,, N, 0

Calculated,%: C 63.42; H 5.82; N 22.22.

Example 5. 5 Amino-2,4-dicyano-2,3-digndrofuran.

Analogously to example 1 of 12.4 g; 4,4,5,5, -tetracyano-2-butyrophenone in 300 ml of water, 2.42 g (23%) of the product was obtained with m.p.

Found,%: C 68.46; H 4.03; N 19.67

C ,, H, N, 0.

Calculated,%: C 68.25; H 4.26; N 19.91.

By reducing the process temperature to 30 ° C, the yield of the target product is somewhat reduced (to 48% under conditions

of Example 1) due to the possible slowdown and incomplete reaction.

Increasing the process temperature to C leads to some

a decrease in the yield of the target product due to its partial burn-up (up to 39% under the conditions of example 1.

Proofreader A.Zimoskorv

Claims (3)

1. METHOD FOR PRODUCING 5-AMINO-2,4-Dicyano-2,3-DIGYDROFURANES of the general formula where R ₍ is a hydrogen atom or lower alkyl; R ₂ is lower alkyl or phenyl; or R, hR ₂ together is trimethylene or tetramethylene, characterized in that the tetracyanketone of the general formula (JN About CN CN where R ₍ and R ₂ have the above meanings, are reacted with hydrogen peroxide in an alkaline environment. 2. The method of pop. 1, with the fact that the process is carried out at 30-63 ° C. * 3. The method of pop. 2, excellent u- | and with the fact that, in order to increase the yield, the process is carried out at 40-45 ° C. Sibanifizi