N-Methylol-alpha-chloroacetamide → 2-Chloro-N-[5-(1,1-dimethylethyl)-3-dimethylaminomethyleneaminosulfonyl-2-hydroxybenzyl]-acetamide

HRID 364893Notes

Reaction equation

HRID 364893 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([S:12]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])(=[O:14])=[O:13])[CH:6]=1)([CH3:4])[CH3:3].[Cl:20][CH2:21][C:22]([NH:24][CH2:25]O)=[O:23]>S(=O)(=O)(O)O>[Cl:20][CH2:21][C:22]([NH:24][CH2:25][C:9]1[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:6]=[C:7]([S:12]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])(=[O:13])=[O:14])[C:8]=1[OH:11])=[O:23]

Participants

4

Reactant 2

HCID 62466N-Methylol-alpha-chloroacetamideHCID 541555634-(1,1-Dimethylethyl)-2-dimethylaminomethyleneaminosulfonylphenol

Product 1

HCID 539481172-Chloro-N-[5-(1,1-dimethylethyl)-3-dimethylaminomethyleneaminosulfonyl-2-hydroxybenzyl]-acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3 g (0.01 mole) of 4-(1,1-dimethylethyl)-2-dimethylaminomethyleneaminosulfonylphenol are dissolved in 30 ml of sulfuric acid, and 1.1 g (0.009 mole) of 2-chloro-N-hydroxymethylacetamide are added. The mixture is stirred for 30 minutes at room temperature and poured into ice water. The product is filtered off with suction and recrystallized from methanol.

Workup

  1. filtrationThe product is filtered off with suction
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-980eab68705a4bee91dfbf1349e936a1
Source dataset
uspto-grants-1986_08
Patent number
US04607030

Reaction notes

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