Chlorosulfonyl isocyanate → HCID 54313059, compound

HRID 342227Notes

Reaction equation

HRID 342227 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[CH2:8]([N:11]([CH3:36])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=2)=O)=[C:21]([NH:34][CH3:35])[CH:20]=1)[CH:9]=[CH2:10].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:8]([N:11]([CH3:36])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:22]([C:25]([C:27]3[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=3)=[N:5][C:6](=[O:7])[N:34]2[CH3:35])=[CH:23][CH:24]=1)[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanate2×HCID 516892Sodium BicarbonateHCID 11113277HCID 11113277, compound

Product 1

HCID 54313059HCID 54313059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

A solution of 0.16 ml of chlorosulphonyl isocyanate in 0.8 ml of methylene chloride is added dropwise at 0° C. to a solution of 0.69 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-methylamino-phenyl]-(4-bromo-phenyl)-methanone in 4 ml of methylene chloride. After 3 hrs. at room temperature the mixture is again cooled to 0° C. and 0.8 ml of chlorosulphonyl isocyanate in 0.5 ml of methylene chloride is added dropwise. After 1 hr. at room temperature the mixture is worked-up with saturated sodium bicarbonate solution/methylene chloride and purified over silica gel with methylene chloride/methanol/25% aqueous ammonium hydroxide (95:5:0.5). There is obtained 0.26 g of 7-[6-(allyl-methyl-amino)-hexyloxy]-4-(4-bromo-phenyl)-1-methyl-1H-quinazolin-2-one, MS: m/e 484 (M+H+, 1 Br).

Workup

  1. waitAfter 1 hr
  2. customat room temperature
  3. custompurified over silica gel with methylene chloride/methanol/25% aqueous ammonium hydroxide (95:5:0.5)

Sources & evidence

ORD record
ord-bee771b0af6f415ebdaa13fe1bc96d1f
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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