Triethylamine → HCID 5329094, compound

HRID 1069023Notes

Reaction equation

HRID 1069023 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:30]([CH:29]=[CH2:28])(=[O:32])=[O:31])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 5329094HCID 5329094, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(3-bromophenyl)-4,6-quinazolindiamine (315 mg, 1 mmol) and triethylamine (0.5 mL) in THF (50 mL) at 0° C. was dropwise added 2-chloroethylsulfonyl chloride (490 mg, 3 mmol). After the solution was stirred at 0° C. for 10 min, it was chromatographed on silica gel with 10% methanol in chloroform to give 212 mg of ethenesulfonic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide as an light yellow solid: HRMS (m/e): M+403.9937. Modified a method from A. A. Goldberg, J. Chem., Soc., 464 (1945).

Workup

  1. customat 0° C.
  2. customit was chromatographed on silica gel with 10% methanol in chloroform

Sources & evidence

ORD record
ord-4e243c6ee6004e5b992880e7f70e317d
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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