Acetone → 4-(Dimethyloctylaminoacetoxy) benzene sulfonic acid

HRID 703758

Reaction equation

HRID 703758 reaction equation
ClC[C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1)=[O:4].[Na].CN(C)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C.[CH3:28]C(C)=O.[CH3:32][C:33]([N:35]([CH3:37])C)=O>>[CH3:28][C:33]([CH3:32])([NH:35][CH2:37][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 5

HCID 180AcetoneHCID 16224DimethyloctylamineHCID 31374DimethylacetamideHCID 5360545SodiumHCID 151139164-(Chloroacetyloxy)benzene sulfonic acid

Product 1

HCID 867445134-(Dimethyloctylaminoacetoxy) benzene sulfonic acid

Procedure

To a stirred slurry of 54.5 g (0.2 mole) of 4-(chloroacetyloxy)benzene sulfonic acid, a sodium salt, in 250 mL of dimethylacetamide was added dropwise over 15 minutes 31.5 g (0.2 mole) of dimethyloctylamine. After stirring for an additional 3 hours, the contents of the flask became a solid mass. This was slurried with 200 mL of acetone, filtered, washed twice with 250 mL potions of acetone and dried at 50°-60° C. under reduced pressure to give 74 g of product. 1H NMR (DMSO-d6) δ0.9 (t, 3H), 1.24 (m, 10H), 1.6 (m, 2H), 3.3 (s, 6H), 3.5 (m 2H), 4.95 (s, 2H), 7.1 (d, 2H), 7.7 (d, 2H).

Workup

  1. filtrationfiltered
  2. washwashed twice with 250 mL potions of acetone
  3. customdried at 50°-60° C. under reduced pressure

Sources & evidence

ORD record
ord-d8af86220fb54e109f69c39ce2b2da9f
Source dataset
uspto-grants-1991_01
Patent number
US04985180

Linked notes

Loading…