Triethylamine → 4-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoic acid cyclopropylamide

HRID 1579703Notes

Reaction equation

HRID 1579703 reaction equation
[CH3:1][N:2]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[N:3]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].Cl.[CH:35]1([NH2:38])[CH2:37][CH2:36]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH:35]1([NH:38][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([CH2:14][N:3]([C:4]([O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:5])[N:2]([CH3:1])[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[CH:16][CH:17]=2)[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11708049Cyclopropylamine hydrochlorideHCID 215690594-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoyl chloride

Product 1

HCID 540207054-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoic acid cyclopropylamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

16.5 g. of 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)methyl]-benzoyl chloride were added to 100 ml. of absolute benzene and treated with 3.1 g. of cyclopropylamine hydrochloride. 7.5 g. of triethylamine and 50 ml. of benzene were then dropped into the reaction mixture at 20°-30° with stirring. The reaction mixture was worked up as in Example 3, yielding 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoic acid cyclopropylamide, the carbobenzoxy groups of which were then removed by treatment with hydrogen bromide/glacial acetic acid. The product, 4-[(2-methyl-hydrazino)-methyl]-benzoic acid cyclopropylamide hydrobromide, melted at 180°-182°.

Sources & evidence

ORD record
ord-384ef8582ae24b9bb6763ff05ebca1b7
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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