2-Thiophenecarboxylic acid, 3-(isocyanatosulfonyl)-, methyl ester → HCID 13369450, compound

HRID 1153945Notes

Reaction equation

HRID 1153945 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[CH:12]=[C:11]([CH3:13])[O:10][C:5]=2[N:6]=[C:7]([NH2:9])[N:8]=1.[C:14]([C:18]1[S:19][CH:20]=[CH:21][C:22]=1[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])([O:16][CH3:17])=[O:15]>C(#N)C>[CH3:1][O:2][C:3]1[C:4]2[CH:12]=[C:11]([CH3:13])[O:10][C:5]=2[N:6]=[C:7]([NH:9][C:27]([NH:26][S:23]([C:22]2[CH:21]=[CH:20][S:19][C:18]=2[C:14]([O:16][CH3:17])=[O:15])(=[O:24])=[O:25])=[O:28])[N:8]=1

Participants

4

Reactant 2

HCID 1572962-Thiophenecarboxylic acid, 3-(isocyanatosulfonyl)-, methyl esterHCID 13369449HCID 13369449, compound

Product 1

HCID 13369450HCID 13369450, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A 0.2 g sample of 4-methoxy-6-methylfuro[2,3-d]pyrimidin-2-amine of Example 8 was stirred in 10 ml of anhydrous acetonitrile while 2.0 ml of a 1M solution of 2-carbomethoxy-3-thiophenesulfonylisocyanate in acetonitrile was added at once. The mixture immediately became homogenous then the solid product crystallized out at ambient temperature and was collected after 1 hour. The yield of product was 0.3 g, m.p. 194°-196°. An NMR (60 MHz) spectrum (CDCl3 /DMSO-d6) exhibited absorptions at 2.5, 4.2, 6.4, 7.3, 7.9, 3.9 (methyl ester), 7.5 and 12.5 (broad NH's) ppm and the infrared spectrum (nujol) exhibited bands at 3100 (NH), 1730 (ester), 1700 (urea) cm-1 indicating the title compound.

Workup

  1. additionwas added at once
  2. customThe mixture immediately became homogenous then the solid product crystallized out at ambient temperature
  3. customwas collected after 1 hour

Sources & evidence

ORD record
ord-7f17fcb69e5241c58d88275385781b35
Source dataset
uspto-grants-1984_12
Patent number
US04487626

Reaction notes

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