Ethyl bromoacetate → HCID 21283681, compound

HRID 2232381Notes

Reaction equation

HRID 2232381 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[CH2:11]([O:13]C(=O)CBr)[CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:1][C:2]1[N:6]([CH2:12][CH2:11][OH:13])[C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 132487922-Methyl-4,5,6,7-tetrahydro-1H-1,3-benzodiazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 21283681HCID 21283681, compound

Procedure

This compound was prepared from 2-methyl-4,5,6,7-tetrahydrobenzimidazole by reaction with ethylbromoacetate followed by reduction with lithium aluminium hydride to give 2-(2-methyl-4,5,6,7-tetrahydrobenzimidazol-1-yl)ethanol. Reaction with ethyl 4-chloroacetoacetate following the procedure of 1 above gave the title compound as a red oil. NMR, CDCl3 : δ 1.26 (t, J=6 Hz, 3H); 1.80 (m, 4H); 2.40 (s, 3H); 2.49 (m, 2H); 2.57 (m, 2H); 3.44 (s, 2H); 3.67 (t, J=5 Hz, 2H); 3.92 (t, J=5 Hz, 2H); 4.13 (s, 2H); 4.20 (q, J=6 Hz, 2H).

Sources & evidence

ORD record
ord-748379c2d9ff420fbcfd668305dfd3bc
Source dataset
uspto-grants-1988_11
Patent number
US04788205

Reaction notes

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