Dimethylamine → HCID 12409664, compound

HRID 1729790Notes

Reaction equation

HRID 1729790 reaction equation
[C:1]([C:9]1[C:17]([NH:18][C:19](=[O:22])[CH2:20][Cl:21])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33]>>[ClH:21].[C:1]([C:9]1[C:17]([NH:18][C:19](=[O:22])[CH2:20][N:32]([CH3:33])[CH3:31])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 12409661HCID 12409661, compound

Product 1

HCID 12409664HCID 12409664, compound

Procedure

A mixture of 4-benzoyl-3-benzyloxy-5-chloroacetamidobenzoic acid (0.85 g) and 20% w/w aqueous dimethylamine (10 ml) is left at room temperature for 20 hours and is then evaporated in vacuo. The residue is triturated with conc. hydrochloric acid (about 5 ml) and the resulting precipitate is collected by filtration and dried. After recrystallization from methyl cellosolve, 4-benzoyl-3-benzyloxy-5-dimethylaminoacetamidobenzoic acid hydrochloride is obtained with a melting point of 264.5°-265.5° C.

Workup

  1. customis then evaporated in vacuo
  2. customThe residue is triturated with conc. hydrochloric acid (about 5 ml)
  3. filtrationthe resulting precipitate is collected by filtration
  4. customdried
  5. customAfter recrystallization from methyl cellosolve

Sources & evidence

ORD record
ord-b2831434a36c4fdd991c616ee113a74e
Source dataset
uspto-grants-1976_11
Patent number
US03989745

Reaction notes

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