Ammonia → N-tert.butyl-3,5-dibromo-2-hydroxy-benzylamine hydrochloride

HRID 616410

Reaction equation

HRID 616410 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:4]([CH:5]=O)[C:3]=1[OH:11].[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].N.[ClH:18]>C(O)C.CCOCC.C(O)=O>[ClH:18].[C:12]([NH:16][CH2:5][C:4]1[CH:7]=[C:8]([Br:10])[CH:9]=[C:2]([Br:1])[C:3]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 70243,5-Dibromosalicylaldehyde

Product 1

HCID 20308288N-tert.butyl-3,5-dibromo-2-hydroxy-benzylamine hydrochloride

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

7 gm of 3,5-dibromo-salicylaldehyde, 17.5 gm of tert. butylamine and 7.7 gm of formic acid were heated for 6 hours at 70°-80° C. Subsequently, the reaction mixture was admixed with aqueous 2 N ammonia, vigorously shaken, and the precipitate formed thereby was sucked off. The residue was dissolved in ethanol, acidified with ethanolic hydrochloric acid and admixed with ether in order to crystallize the product out. N-tert.butyl-3,5-dibromo-2-hydroxy-benzylamine hydrochloride, m.p. 216°-220° C (decomp.), was obtained after recrystallization from absolute ethanol/ether.

Workup

  1. customthe precipitate formed
  2. customto crystallize the product out

Sources & evidence

ORD record
ord-3136111fc16f4cebb7a7f3363b4d7f1b
Source dataset
uspto-grants-1978_02
Patent number
US04073942

Linked notes

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