Hydrogen Bromide → 4-[(2-Methylhydrazino)-methyl]-benzoic acid [2-hydroxy-3,3,3-trichloropropyl]amide hydrobromide

HRID 1579711Notes

Reaction equation

HRID 1579711 reaction equation
C[N:2]([C:24](OCC1C=CC=CC=1)=O)[N:3]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)C(OCC1C=CC=CC=1)=O.C(Cl)Cl.[OH:37][CH:38]([C:41]([Cl:44])([Cl:43])[Cl:42])[CH2:39][NH2:40].[BrH:45]>C(O)(=O)C.O>[BrH:45].[OH:37][CH:38]([C:41]([Cl:44])([Cl:43])[Cl:42])[CH2:39][NH:40][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:3][NH:2][CH3:24])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 6344Dichloromethane2×HCID 215437Propanol, 3-amino-1-trichloro-HCID 215690594-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoyl chloride

Product 1

HCID 1317098904-[(2-Methylhydrazino)-methyl]-benzoic acid [2-hydroxy-3,3,3-trichloropropyl]amide hydrobromide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

15.8 g. of 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)methyl]-benzoyl chloride were dissolved in 50 ml. of methylene chloride. This solution was added, while stirring, dropwise to a suspension of 12.6 g. of 2-hydroxy-3,3,3-trichloro-propylamine in 150 ml. of methylene chloride. Stirring was continued for 2 hours at room temperature and 30 minutes at 40°, whereupon 50 ml. of water were added thereto. The product was worked up according to Example 3 and treated with hydrogen bromide in glacial acetic acid. The crystalline crude material was recrystallized from ethanol/acetonitrile/ether, yielding 4-[(2-methylhydrazino)-methyl]-benzoic acid [2-hydroxy-3,3,3-trichloropropyl]amide hydrobromide melting at 187°-189° (dec.).

Workup

  1. additionThis solution was added
  2. stirringStirring
  3. customThe crystalline crude material was recrystallized from ethanol/acetonitrile/ether

Sources & evidence

ORD record
ord-ad9b02f778a642cdb976f29f13b2393d
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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