Bromo-4'-chloro-3'-sulfamoylacetophenone → HCID 22760495, compound

HRID 1703879Notes

Reaction equation

HRID 1703879 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:6]=1)=[O:4].[CH2:16]([NH:18][C:19]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)=[S:20])[CH3:17]>C(OCC)C>[CH2:16]([N:18]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:6]=2)([OH:4])[CH2:2][S:20][C:19]1=[N:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[CH3:17]

Participants

4

Reactant 2

HCID 12952390Bromo-4'-chloro-3'-sulfamoylacetophenoneHCID 19686552HCID 19686552, compound

Product 1

HCID 22760495HCID 22760495, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.7 g of 2-bromo-4'-chloro-3'-sulfamoylacetophenone and 3 g of 1-ethyl-3-(2-pyridylmethyl)-thiourea were reacted according to the prescription given in Example 23 and 150 ml of diethyl ether were added to the reaction mixture. The hygroscopic 3-ethyl-4-(4-chloro-3-sulfamoylphenyl)-2-(2-pyridylmethylimino)-1,3-thiazolidine-4-ol-hydrobromide which had separated as crystals was rapidly filtered off, dissolved in 50 ml of water and converted into the end product as described in Example 28. Colorless solid body, decomposition beginning at 135° C., γC=N 1615 cm-1.

Workup

  1. additionwere added to the reaction mixture
  2. customThe hygroscopic 3-ethyl-4-(4-chloro-3-sulfamoylphenyl)-2-(2-pyridylmethylimino)-1,3-thiazolidine-4-ol-hydrobromide which had separated as crystals
  3. filtrationwas rapidly filtered off
  4. dissolutiondissolved in 50 ml of water
  5. customat 135° C.

Sources & evidence

ORD record
ord-11be9a6f3f534fceba4d4e2707ad6e9e
Source dataset
uspto-grants-1978_11
Patent number
US04125614

Reaction notes

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