Dimethylamine → HCID 20033708, compound

HRID 231681Notes

Reaction equation

HRID 231681 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[S:18][C:17]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(O)=[O:2].[C:23](N1C=CN=C1)([N:25]1C=CN=[CH:26]1)=O.CNC.C(NC(CC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1)=O)C.CNC(CCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1)=O.CN(C)C(CCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1)=O>O1CCCC1>[CH3:23][N:25]([CH3:26])[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[S:18][C:17]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)=[O:2]

Participants

8

Reactant 6

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 20033691HCID 20033691, compoundHCID 20033697HCID 20033697, compoundHCID 20033730HCID 20033730, compoundHCID 20033735HCID 20033735, compound

Product 1

HCID 20033708HCID 20033708, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-carboxymethylphenylsulfonyl)thiophene-2-sulfonamide (1.6 g) was dissolved in 50 ml of tetrahydrofuran and 0.72 g of carbonyldiimidazole was added. After stirring for one hour at room temperature excess aqueous dimethylamine was added and the mixture stirred overnight. The reaction mixture was concentrated under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was separated, dried over sodium sulfate and concentrated under vacuum, giving an oil weighing 1.35 g, N.M.R. (acetone, d6) δ: 2.92 (3H, s), 3.08 (3H, s), 3.84 (2H, s), 7.02 (2H, s), 7.50 (3H, m), 7.65 (1H, d), 7.90 (2H, d). The following compounds were also made by similar procedures: 5-(4-ethylcarbamoylmethylphenylsulfonyl)thiophene-2-sulfonamide, 5-[4-(2-methylcarbamoylethyl)phenylsulfonyl]thiophene-2-sulfonamide, and 5-[4-(3-dimethylcarbamoylpropyl)phenylsulfonyl]thiophene-2-sulfonamide.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customgiving an oil

Sources & evidence

ORD record
ord-b175ae911c3b44c9a9aa819c313750a0
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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