Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → HCID 20251497, compound

HRID 1284409Notes

Reaction equation

HRID 1284409 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][F:9])[N:5]=[C:4]([NH2:10])[N:3]=1.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])([O:13][CH3:14])=[O:12]>C(Cl)Cl>[F:9][CH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([NH:10][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:23])=[O:22])=[O:26])[N:5]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 20251499HCID 20251499, compound

Product 1

HCID 20251497HCID 20251497, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-methyl-6-fluoromethyl-2-pyrimidinamine (1.4 mmol) in 25 ml of CH2Cl2 was added o-carbomethoxybenzenesulfonyl isocyanate (1.77 mmol). After stirring 16 hours the reaction was concentrated and the resulting solid washed with butyl chloride to afford 0.28 g of the desired product, m.p. 181°-186° C. NMR (90 MHz, CDCl3): δ 2.5 (s, 3H); 4.0 (s, 3H); 5.2 (s, 1H); 5.7 (s, 1H); 7.0 (s, 1H); 7.6 (m, 3H); 8.2 (m, 1H); 10.3 (s, 1H); 12.8 (br. s, 1H).

Workup

  1. concentrationwas concentrated
  2. washthe resulting solid washed with butyl chloride

Sources & evidence

ORD record
ord-353e53c6eaad4d11abd6eeb2c7b12553
Source dataset
uspto-grants-1986_01
Patent number
US04563211

Reaction notes

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