2-Carbamoylmethoxy-4-{(5-methoxy-2-nitrophenyl)aminosulfonyl}phenoxyacetamide → 2-Carbamoylmethoxy-4-{(5-methoxy-2-aminophenyl)aminosulfonyl}phenoxyacetamide

HRID 1593255Notes

Reaction equation

HRID 1593255 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:16]=[C:15]([S:17]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=2[N+:29]([O-])=O)(=[O:19])=[O:18])[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([NH2:12])=[O:11])(=[O:3])[NH2:2]>CC(N(C)C)=O.[Pt]=O>[C:1]([CH2:4][O:5][C:6]1[CH:16]=[C:15]([S:17]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=2[NH2:29])(=[O:19])=[O:18])[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([NH2:12])=[O:11])(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 589992342-Carbamoylmethoxy-4-{(5-methoxy-2-nitrophenyl)aminosulfonyl}phenoxyacetamide

Product 1

HCID 589992402-Carbamoylmethoxy-4-{(5-methoxy-2-aminophenyl)aminosulfonyl}phenoxyacetamide

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 31374DimethylacetamideSolvent

Procedure

2-Carbamoylmethoxy-4-{(5-methoxy-2-nitrophenyl)aminosulfonyl}phenoxyacetamide (Intermediate A67, 14 g, 0.031 mol) in 100 mL of dimethylacetamide was hydrogenated with platinum oxide (0.50 g, 0.0022 mol) as catalyst. After the catalyst was filtered off, the mixture was concentrated under high vacuum. The residue was triturated successively with 1:1 hexanes:ethyl acetate and 2:1 dichloromethane:hexanes. The collected solid, title compound, weighed 12.8 g (97%) after air-drying.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe mixture was concentrated under high vacuum
  3. customThe residue was triturated successively with 1:1 hexanes
  4. customafter air-drying

Sources & evidence

ORD record
ord-01e306ae355b4c4c886afe22ee0d6f6e
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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