Dimethylamine → HCID 20261694, compound

HRID 465047Notes

Reaction equation

HRID 465047 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].Cl[CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[N+:17]([O-])(O)=O.[CH3:21][NH:22][CH3:23].[CH2:24]([N:26](CC)CC)[CH3:25]>O1CCCC1.[C].[Pd].C(O)(=O)C.C1(C)C(C)=CC=CC=1>[C:24]([CH2:25][CH2:2][CH2:3][O:4][C:14]1[CH:15]=[CH:16][C:11]2[N:10]=[C:8]([CH2:7][N:22]([CH3:23])[CH3:21])[NH:17][C:12]=2[CH:13]=1)#[N:26]

Participants

10

Reactant 5

HCID 674DimethylamineHCID 944Nitric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11485Chloroacetanilide

Product 1

HCID 20261694HCID 20261694, compound

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Then, the product sodium salt was made to react with 4-chlorobutyl nitrile (58 g) for 48 hrs at 50° C. to yield 4-(4-nitrophenoxy)butylnitrile (51 g). This nitro compound (16 g) was reduced under pressure of 70 atm in tetrahydrofuran (140 ml) using 5% palladium carbon as a catalyst. Then, with the addition of triethylamine (9.83 g), the product was made-react with chloroacetylchloride (11 g)-yield 4-(3-cyanopropyl)oxychloroacetanilide (18.5 g). The thus obtained chloroacetanilide compound (9.2 g) was nitrated by nitric acid (specific weight 1.42 3.8 ml) in acetic acid (90 ml) and, after a reaction with dimethylamine, the nitrated product as subjected to a reduction under the pressure of 70 atm, followed by a ring closure with heating in xylene (200 ml) to yield 5-[(3-cyanopropyl)oxy]-2-dimethylaminomethylbenzimidazole (5.9 g) as a light brown oil product.

Sources & evidence

ORD record
ord-57dca6d6120b46fab78104dfbdfb93bc
Source dataset
uspto-grants-1985_10
Patent number
US04550118

Reaction notes

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