Hexamethylenetetramine → 4-(Aminoacetyl)phenoxyacetic acid hydrochloride

HRID 2419363Notes

Reaction equation

HRID 2419363 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].C1N2CN3CN(C2)C[N:17]1C3.C(Cl)(Cl)[Cl:27]>>[ClH:27].[NH2:17][CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 49662-[4-(2-bromoacetyl)phenoxy]acetic AcidHCID 6212Chloroform

Product 1

HCID 145369464-(Aminoacetyl)phenoxyacetic acid hydrochloride

Procedure

A solution of 4-(bromoacetyl)phenoxyacetic acid (26g.) in chloroform (150ml.) was stirred as hexamine (14g.) was added. The mixture was stirred at room temperature for 3 days and then filtered. The solid was suspended in ethanol (250ml.), concentrated hydrochloric acid (50ml.) was added and the mixture stirred at room temperature for 18 hours. The mixture was then filtered and the filtrate diluted with diethyl ether (1,500ml.). The solid so produced was filtered off, washed with a mixture of ethanol and diethyl ether to give 4-(aminoacetyl)phenoxyacetic acid hydrochloride, m.p. > 250° C. N.m.r. δ 7.0-7.14, 7.92-8.06 each 2H (aromatic protons), 4.5 (2H, N⊕H3CH2CO) and 4.81 (2H, --OCH2.COOH).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. additionconcentrated hydrochloric acid (50ml.) was added
  4. stirringthe mixture stirred at room temperature for 18 hours
  5. filtrationThe mixture was then filtered
  6. additionthe filtrate diluted with diethyl ether (1,500ml.)
  7. customThe solid so produced
  8. filtrationwas filtered off
  9. washwashed with a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-ef1b3ff3ce1e48788c1d9ae24bc2004c
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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