Butyl Chloride → HCID 13937617, compound

HRID 648853Notes

Reaction equation

HRID 648853 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[CH2:14][S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16])=[O:4].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([NH2:31])[N:24]=1.C(Cl)CCC>C(Cl)Cl>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([NH:31][C:19]([NH:18][S:15]([CH2:14][C:6]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:17])=[O:16])=[O:20])[N:24]=1

Participants

5

Reactant 3

HCID 8005Butyl ChlorideHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 13937616HCID 13937616, compound

Product 1

HCID 13937617HCID 13937617, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the sulfonyl isocyanate from Example 6 (approximately 1.2 g) and 0.55 g of 4,6-dimethoxy-2-aminopyrimidine in 5 ml methylene chloride was stirred at room temperature for 4 hours. The reaction mixture was then filtered and the filtrate concentrated in vacuo to give a gummy solid. Trituration with warm n-butyl chloride gave a tan solid which was filtered and washed with ethyl acetate. The yield of 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]methyl-3-nitrobenzoic acid, methyl ester was 1.0 g as a light tan-colored solid, m.p. 177°-181°; IR(nujol): 1730, 1700 cm-1 ; NMR (CDCl3 /DMSO-d6): δ 3.75 (6H, s, OCH3 's), 3.8 (3H, s, CO2CH3), 5.7 (2H, s, --CH2 --), 5.8 (1H, s, heterocyclic ring H), 7.65-8.4 (3H, m).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give a gummy solid
  4. filtrationwas filtered
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-512ee11d2e0e45ba8c15ec41379b7cc7
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

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