Hydrochloric Acid → 2-Acetyl-N-[(4-methylquinazolin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1155944Notes

Reaction equation

HRID 1155944 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([NH:12][C:13]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([OH:27])=O)(=[O:18])=[O:17])=[O:14])[N:3]=1.[CH3:28][Li].O.Cl>O1CCCC1.CCOCC.C(Cl)Cl>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:16]([NH:15][C:13]([NH:12][C:4]1[N:3]=[C:2]([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:14])(=[O:18])=[O:17])(=[O:27])[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 20536263N-[(4-Methylquinazolin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamideHCID 178418348HCID 178418348, compound

Product 1

HCID 205362592-Acetyl-N-[(4-methylquinazolin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 0.86 g of N-[(4-methylquinazolin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide in 50 ml of anhydrous tetrahydrofuran is treated with 40 ml of a 1.4 M solution of methyllithium in ether at 25° under a nitrogen atmosphere. The mixture is stirred for 4 hours at ambient temperature and then poured into 500 ml of water containing 10 ml of concentrated hydrochloric acid. The product can be isolated by extraction into methylene chloride followed by evaporation and if necessary, can be purified by preparative thin layer chromatography and/or recrystallization.

Workup

  1. customfollowed by evaporation
  2. customif necessary, can be purified by preparative thin layer chromatography and/or recrystallization

Sources & evidence

ORD record
ord-6e969edd3f8444ca9ced5c613cc35a6d
Source dataset
uspto-grants-1982_06
Patent number
US04333760

Reaction notes

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